1,1-环己基二乙酸单甲酯 | 60142-94-1

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1,1-环己基二乙酸单甲酯
• 英文名称: (1-methoxycarbonylmethylcyclohexyl)acetic acid
• 英文别名: cyclohexylidenedi-acetic acid monomethyl ester；Cyclohexylidendi-essigsaeure-monomethylester；1,1-cyclohexanediacetic acid monomethyl ester；1-Methoxycarbonylmethylcyclohexylacetic acid；monomethyl 1,1-cyclohexane-diacetate；1,1-Cyclohexanediacetic acid mono methyl ester；2-[1-(2-methoxy-2-oxoethyl)cyclohexyl]acetic acid
• CAS: 60142-94-1
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: VLFQWYHVTAGEQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-环己基二乙酸单甲酯 在 dicyclohexyldicarboximide 、 硫酸 、 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 (2S)-2-benzyloxycarbonylamino-5-((1-methoxycarbonylmethylcyclohexyl)acetylperoxy)-5-oxopentanoic acid benzyl ester
  参考文献：
  名称：

  Synthesis of Oxytocin Analogues with Replacement of Sulfur by Carbon Gives Potent Antagonists with Increased Stability

  摘要：

  The neuropeptide oxytocin 1 controls mammary and uterine smooth muscle contraction. Atosiban 2, an oxytocin antagonist, is used for prevention of preterm labor and premature birth. However, the metabolic lifetimes of such peptide drugs are short because of in vivo degradation. Facile production of oxytocin analogues with varying ring sizes wherein sulfur is replaced by carbon (methylene or methine) could be achieved by standard solid-phase peptide synthesis using olefin-bearing amino acids followed by on-resin ring-closing metathesis (RCM). These were tested for agonistic and antagonistic uteronic activity using myometrial strips taken from nonpregnant female rats. Peptide 8 showed agonistic activity in vitro (EC50 = 1.4 x 10(3) +/- 4.4 x 10(2) nM) as compared to 1 (EC50 = 7.0 +/- 2.1 nM). Atosiban analogues 17 (pA(2) = 7.8 +/- 0.1) and 18 (pA(2) 8.0 +/- 0.1) showed substantial activity compared to the parent oxytocin antagonist 2 (pA(2) = 9.9 +/- 0.3). Carba analogue 35 (pA(2) = 6.1 +/- 0.1) had an agonistic activity over 2 orders of magnitude less than its parent 3 (8.8 +/- 10.5). A comparison of biological stabilities of 1,6-carba analogues of both an agonist 8 and antagonist 18 versus parent peptides 1 and 2 was conducted. The half-lives of peptides 8 and 18 in rat placental tissue were shown (Table 2) to be greatly improved versus their parents oxytocin 1 and atosiban 2, respectively. These results suggest that peptides 8 and 18 and analogues thereof may be important leads into the development of a long-lasting, commercially available therapeutic for initiation of parturition and treatment of preterm labor.

  DOI：

  10.1021/jo050539l
• 作为产物：
  描述：

  1,1-环己基二乙酸 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 1,1-环己基二乙酸单甲酯
  参考文献：
  名称：

  Synthesis of Oxytocin Analogues with Replacement of Sulfur by Carbon Gives Potent Antagonists with Increased Stability

  摘要：

  The neuropeptide oxytocin 1 controls mammary and uterine smooth muscle contraction. Atosiban 2, an oxytocin antagonist, is used for prevention of preterm labor and premature birth. However, the metabolic lifetimes of such peptide drugs are short because of in vivo degradation. Facile production of oxytocin analogues with varying ring sizes wherein sulfur is replaced by carbon (methylene or methine) could be achieved by standard solid-phase peptide synthesis using olefin-bearing amino acids followed by on-resin ring-closing metathesis (RCM). These were tested for agonistic and antagonistic uteronic activity using myometrial strips taken from nonpregnant female rats. Peptide 8 showed agonistic activity in vitro (EC50 = 1.4 x 10(3) +/- 4.4 x 10(2) nM) as compared to 1 (EC50 = 7.0 +/- 2.1 nM). Atosiban analogues 17 (pA(2) = 7.8 +/- 0.1) and 18 (pA(2) 8.0 +/- 0.1) showed substantial activity compared to the parent oxytocin antagonist 2 (pA(2) = 9.9 +/- 0.3). Carba analogue 35 (pA(2) = 6.1 +/- 0.1) had an agonistic activity over 2 orders of magnitude less than its parent 3 (8.8 +/- 10.5). A comparison of biological stabilities of 1,6-carba analogues of both an agonist 8 and antagonist 18 versus parent peptides 1 and 2 was conducted. The half-lives of peptides 8 and 18 in rat placental tissue were shown (Table 2) to be greatly improved versus their parents oxytocin 1 and atosiban 2, respectively. These results suggest that peptides 8 and 18 and analogues thereof may be important leads into the development of a long-lasting, commercially available therapeutic for initiation of parturition and treatment of preterm labor.

  DOI：

  10.1021/jo050539l

文献信息

• Process For Synthesis Of Gabapentin
  申请人：Kumar Ashok

  公开号：US20080103334A1

  公开（公告）日：2008-05-01

  A process for preparation of gabapentin comprising a step of obtaining 1,1-cyclohexane diacetic acid monoamide from 1,1-cyclohexane diacetic acid anhydride, wherein said reaction is characterized by the use of ammonia precursor or pre-generated ammonia-isopropanol solution. The invention further discloses preparation of gabapentin and isolation of gabapentin in polymorphic Form II with high yield and purity.

  制备加巴喷丁的方法包括从1,1-环己烷二乙酸酐获得1,1-环己烷二乙酸单酰胺的步骤，其中该反应的特点是使用氨的前体或预生成的氨-异丙醇溶液。该发明还揭示了加巴喷丁的制备以及高产率和纯度下的多形式II加巴喷丁的分离。
• [EN] CYCLIC AMIDES AND IMIDES HAVING SELECTIVE ANTAGONIST ACTIVITY AT ALPHA-1D ADRENERGIC RECEPTOR<br/>[FR] AMIDES ET IMIDES CYCLIQUES POSSEDANT UNE ACTIVITE ANTAGONISTE SELECTIVE AU NIVEAU DU RECEPTEUR ADRENERGIQUE 1D
  申请人：RECORDATI CHEM PHARM

  公开号：WO2001005765A1

  公开（公告）日：2001-01-25

  Compounds (I) R and R1 independently = H or C1-C4 alkyl or together = (CH2)2-6, n=0 or 1, ...... is a single or a double bond, A=CO or CH2, A1 represents a CO or CH2 or CH, each R3 independently = H or C1-C4 alkyl, B is B1 or B2 (B2); Y=N or CH, R2 = halogen, C1-C4 alkyl or CN, R5 = halogen, C1-C4 alkyl, polyfluoroalkyl or NO2, R6 = H or halogen, m is 1 to 3, Z = O, S, NH or NMe) interact selectively with the α1D subtype of the α1 adrenergic receptor. This selectively makes these compounds useful agents in tissues particularly rich in α1D adrenergic receptors, thus useful in reducing contractility of an unstable urinary bladder, in the treatment and prevention of atherosclerosis as they are inhibitors of noradrenaline-mediated cell proliferation in smooth muscles, and in reducing vascular adrenergic tone. The preparation of these compounds, their enantiomers, diastereoisomers, N-oxides and pharmaceutically acceptable salts, and pharmaceutical compositions containing them are also claimed.

  化合物（I）中，R和R1分别为H或C1-C4烷基，或者在一起为（CH2）2-6，n=0或1，......为单键或双键，A=CO或CH2，A1代表CO或CH2或CH，每个R3独立地为H或C1-C4烷基，B为B1或B2（B2）；Y=N或CH，R2=卤素，C1-C4烷基或CN，R5=卤素，C1-C4烷基，多氟烷基或NO2，R6=H或卤素，m为1到3，Z=O，S，NH或NMe）与α1D亚型的α1肾上腺素受体选择性相互作用。这种选择性使得这些化合物在α1D肾上腺素受体特别丰富的组织中成为有用的药物，因此可用于减少不稳定的膀胱的收缩性，在动脉粥样硬化的治疗和预防中，因为它们是平滑肌中去甲肾上腺素介导的细胞增殖的抑制剂，以及减少血管肾上腺素张力。还声明了这些化合物、它们的对映体、对映异构体、N-氧化物和药学上可接受的盐的制备以及含有它们的制药组合物。
• 2-pyrrolidinone derivatives substituted at position 4 for reducing the extracellular glutamate level
  申请人：——

  公开号：US20020173537A1

  公开（公告）日：2002-11-21

  2-pyrrolidinone derivatives which have in position 4 at least one substituent are described herein. Methods of treating polygltamine disorders such as Huntington's disease, dentorubropallidoluysian atrophy (DRPLA), spinal and bulbar muscular atrophy (SBMA), and spinocerebellar ataxias with 2-pyrrolidinone derivatives are also descibed.

  本文描述了在位置4上至少有一个取代基的2-吡咯烷酮衍生物。还描述了使用2-吡咯烷酮衍生物治疗多谷氨酸疾病，如亨廷顿病，牙状核红核苍白球体萎缩症（DRPLA），脊髓和延髓肌肉萎缩症（SBMA）和小脑共济失调症的方法。
• Novel 4-(2-furoyl) aminopiperidines, intermediates in synthesizing the same, process for producing the same and medicinal use of the same
  申请人：Fukutomi Ryuuta

  公开号：US20050085508A1

  公开（公告）日：2005-04-21

  There are provided novel 4-(2-furoyl)aminopiperidines represented by the general formula (I), their synthetic intermediates, processes for their preparation and medicaments containing them. In the above formula, X is CH or N, and Y is a group of the following general formula (II), formula (II-a) or formula (III): wherein a, b and c are each an integer of 0-6; Z is CH 2 or NH; W is O or S; T is O or N—R 15 wherein R 15 is H, a C1-C6 alkyl group, a benzyl group or a phenethyl group; and R 1 is H, a C1-C6 alkoxycarbonyl group, a benzyloxycarbonyl group, or the like. The 4-(2-furoyl)aminopiperidine derivatives according to this invention possess opioid μ antagonistic activity and are useful for the treatment or prevention of side effects which are caused by μ receptors agonist and which are selected from constipation, nausea/emesis or itch, or for the treatment or prevention of idiopathic constipation, postoperative ileus, paralytic ileus, irritable bowel syndrome or chronic pruritus.

  提供了一种新的4-(2-呋喃酰基)氨基哌啶化合物，其通式表示为(I)，以及它们的合成中间体、制备过程和含有它们的药物。 在上述式中，X为CH或N，Y为以下通式(II)、式(II-a)或式(III)的基团： 其中a、b和c均为0-6的整数；Z为CH2或NH；W为O或S；T为O或N—R15，其中R15为H、C1-C6烷基、苄基或苯乙基；R1为H、C1-C6烷氧羰基、苄氧羰基或类似基团。本发明所述的4-(2-呋喃酰基)氨基哌啶衍生物具有阿片μ受体拮抗活性，可用于治疗或预防由μ受体激动剂引起的副作用，包括便秘、恶心/呕吐或瘙痒，或用于治疗或预防特发性便秘、术后肠梗阻、麻痹性肠梗阻、肠易激综合征或慢性瘙痒。
• 2-Pyrrolidinone derivatives substituted at position 4 for reducing the extracellular glutamate level
  申请人：Feuerstein J. Thomas

  公开号：US20050228035A1

  公开（公告）日：2005-10-13

  2-pyrrolidinone derivatives which have in position 4 at least one substituent are described herein. Methods of treating polyglutamine disorders such as Huntington's disease, dentorubropallidoluysian atrophy (DRPLA), spinal and bulbar muscular atrophy (SBMA), and spinocerebellar ataxias with 2-pyrrolidinone derivatives are also descibed.

  本文描述了在位置4上至少有一个取代基的2-吡咯烷酮衍生物。还描述了使用2-吡咯烷酮衍生物治疗多谷氨酸疾病，如亨廷顿病、牙齿红核球纤维化性萎缩症（DRPLA）、脊髓和球状体肌萎缩症（SBMA）以及小脑共济失调的方法。