(1-ethoxycarbonyl-2-oxo-cyclohexyl)-acetic acid ethyl ester | 7251-30-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1-ethoxycarbonyl-2-oxo-cyclohexyl)-acetic acid ethyl ester
• 英文别名: (+/-)-1-Aethoxycarbonylmethyl-2-oxo-cyclohexancarbonsaeure-aethylester；(1-Aethoxycarbonyl-2-oxo-cyclohexyl)-essigsaeure-aethylester；Ethyl 1-(2-ethoxy-2-oxoethyl)-2-oxocyclohexane-1-carboxylate
• CAS: 7251-30-1
• 化学式: C₁₃H₂₀O₅
• 分子量: 256.299
• InChiKey: JEGLGZDLMRRJMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1-ethoxycarbonyl-2-oxo-cyclohexyl)-acetic acid ethyl ester 在 盐酸 、 sodium hydroxide 作用下， 生成 hexane-1,2,6-tricarboxylic acid trimethyl ester
  参考文献：
  名称：

  Fat embolism syndrome and elective knee arthroplasty

  摘要：

  Purpose: To report a case of fat embolism syndrome (FES) following elective left knee arthroplasty and review the diagnosis, investigation, prevention and perioperative management of this condition.Clinical features: A 76-yr-old lady presented for left total knee arthroplasty under general anesthesia. After an uneventful anesthetic and initial recovery, she developed respiratory and neurological complications six hours postoperatively necessitating supportive care in the intensive care unit. Following extensive investigation, a clinical diagnosis of FES was made 48 hr postoperatively supported by the development of diffuse encephalopathy, thrombocytopenia, hypoxemia, chest petechiae and chest x-ray changes. A magnetic resonance imaging scan five days postoperatively confirmed this diagnosis. Her postoperative course showed gradual improvement consistent with a slowly resolving encephalopathy.Previous published cases of FES associated with knee arthroplasty present either with intraoperative cardiorespiratory collapse or, as with this patient, in the postoperative period with respiratory, cardiovascular and/or cerebral dysfunction.Conclusions: The clinical diagnosis of FES is essentially one of exclusion, supported by laboratory and radiological investigations. Preoperative identification of at-risk patients, use of appropriate invasive perioperative monitoring and modified surgical techniques may minimize the development of the syndrome. Treatment is supportive.

  DOI：

  10.1007/bf03020414
• 作为产物：
  描述：

  ethyl 2-(trimethylsilyloxy)cyclohex-1-enecarboxylate 在 copper acetylacetonate 、 四乙基氟化铵水合物 作用下， 以 四氢呋喃 为溶剂， 生成 (1-ethoxycarbonyl-2-oxo-cyclohexyl)-acetic acid ethyl ester
  参考文献：
  名称：

  重氮乙酸乙酯与β-酮酯反应中依赖于催化剂的机理

  摘要：

  在β-酮酸酯的存在下，重氮乙酸乙酯的催化分解产生区域异构的烯醇醚，以及从正式类胡萝卜素插入α-CH键中形成的二酯。产品分布非常依赖催化剂。

  DOI：

  10.1016/s0040-4039(00)99330-4

文献信息

• Construction of Functionalized Carbocycles Having Contiguous Tertiary Carbinol and All-Carbon Stereogenic Centers
  作者：Chennakesava Reddy、Srinivasarao Arulananda Babu、Nayyar Ahmad Aslam、Vadla Rajkumar

  DOI：10.1002/ejoc.201201382

  日期：2013.4

  A highly stereoselective protocol is reported for customizing functionalized carbocyclic building blocks (β-hydroxy esters) and bicyclic lactones with a stereoarray that contains contiguous tertiary carbinol and all-carbon stereocenters. The efficient asymmetric induction and diastereofacial selective addition of allyl and propargyl indiums to hindered α,α-disubstituted cycloalkanones is presented

  报告了一种高度立体选择性的协议，用于定制功能化碳环结构单元（β-羟基酯）和双环内酯，其立体阵列包含连续的叔甲醇和全碳立体中心。介绍了烯丙基和炔丙基铟与受阻 α,α-二取代环烷酮的有效不对称诱导和非对映选择性加成。代表性产物的立体化学是从单晶 X 射线晶体结构分析中明确建立的，并提出了一种合理的反应途径来支持高非对映面选择性。
• Indium-assisted aluminium-based stereoselective allylation of prostereogenic α,α-disubstituted cycloalkanones and imines
  作者：Chennakesava Reddy、Srinivasarao Arulananda Babu、Nayyar Ahmad Aslam

  DOI：10.1039/c4ra04293j

  日期：——

  Al0 for the allylation of a variety of prostereogenic α,α-disubstituted (hindered) cycloalkanones, 1,2-dione-based systems and various imino systems (CN functional groups) is reported. The stereoselective InCl3-catalyzed Al-based allylation of various 2-substituted-2-carbethoxycycloalkanones gave the corresponding products with moderate to excellent diastereoselectivity. The allylation and propargylation

  催化量的InCl 3和Al 0的组合用于烯丙基化各种促成α，α-二取代（受阻）的环烷酮，1,2-二酮基体系和各种亚氨基体系（C N官能团）的烯丙基化被报道。各种2-取代的-2-碳乙氧基环烷酮的立体选择性InCl 3催化的基于Al的烯丙基化，给出了具有中等至优异的非对映选择性的相应产物。使用催化量的InCl 3与Al 0结合使用，使包括α-亚氨基酯在内的亚胺的烯丙基化和炔丙基化得到中等至良好收率的相应的烯丙基化和炔丙基化化合物。如果将γ-取代的烯丙基卤化物添加到亚氨基化合物中，则获得低至非常好的非对映选择性。手性N-叔丁基亚磺酰基亚胺系统的烯丙基化以中等收率提供了相应的产物，具有良好或优异的非对映选择性。
• Ranu, Brindaban C.; Bhar, Sanjay, Journal of the Chemical Society. Perkin transactions I, 1992, # 3, p. 365 - 368
  作者：Ranu, Brindaban C.、Bhar, Sanjay

  DOI：——

  日期：——
• New Route to 7a-Angularly Substituted Hydroindoles
  作者：Kunihiko Mohri、Yuki Yoshida、Shin-ichiro Mataga、Yohko Hisatsune、Kimiaki Isobe、Yoshisuke Tsuda

  DOI：10.3987/com-97-7977

  日期：——

  Strecker type reaction of ethyl 2-oxocyclohexaneacetate with sodium cyanide and ammonium acetate gave 7a-cyano-octahydro-cis-1H-indol-2-one (2a) as a single product, which was alkylated to the N-alkyl derivatives. The cyano group in 2a was convertible to ethoxycarbonylmethyl group by reaction with the Reformatsky reagent generated from ethyl bromoacetate, In the case of the N-methyl derivative 2b, the cyano group was transformed into ethoxycarbonylacetyl group under the same reaction conditions.
• Syntheses of the terpenoid precursors cyclopent-2-enone and cyclohex-2-enone diesters
  作者：I. Kádas、V. Morvai、G. Árvai、L. Tőke、Á. Szöllősy、G. Tóth、M. Bihari

  DOI：10.1007/bf00811764

  日期：1995.1

  Two reaction pathways were elaborated for the practical and convenient synthesis of the title compounds: The first route applies a bromination-dehydrobromination sequence to introduce the double bond into 1-alkoxycarbonyl-2-oxocycloalkylacetic and propionic esters (4a-c, 7a,b). The application of 2,6-lutidine for dehydrobromination of alpha-bromocycloalkanones diesters (5a-c, 8a, b) provides sufficient selectivity to carry out this step without affecting the sensitive ester group. Alternative pathways, involving Michael reaction of diethyl 2-acetylsuccinate or -glutarate with acrolein and subsequent intramolecular aldol condensation, are presented in the case of cyclohex-2-enone derivatives 2a, b.