4-methylcyclohex-3-en-1-ol | 51422-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylcyclohex-3-en-1-ol
• 英文别名: 4-methyl-3-cyclohexenol；4-methyl-3-cyclohexen-1-ol
• CAS: 51422-70-9
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: SHRVHWWZRZPZFL-UHFFFAOYSA-N

物化性质

• 沸点：
  89 °C(Press: 26 Torr)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methylcyclohex-3-en-1-ol 在 Crabtree's catalyst 氢气 作用下， 以 二氯甲烷 为溶剂， 生成 trans-4-Methylcyclohexanol
  参考文献：
  名称：

  用铱催化剂进行羟基定向的烯烃加氢。催化剂的文献：底物化学计量作为反应非对映选择中的变量。

  摘要：

  本研究证明了以下事实：用阳离子铱催化剂Ir（COD）py（PCy 3）PF 6进行的环状和无环烯烃醇的羟基定向加氢表现出反应非对映选择性，这取决于催化剂-基质的化学计量。

  DOI：

  10.1016/s0040-4039(01)91220-1
• 作为产物：
  描述：

  2-methyl-2-vinylcyclobutanone 在 potassium ethoxide 、 甲基锂 、 L-Selectride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 7.0h， 以72%的产率得到4-methylcyclohex-3-en-1-ol
  参考文献：
  名称：

  通过乙烯基环丁烷的烷氧基加速重排进行环己烯醇环化

  摘要：

  2-乙烯基环丁醇的锂盐和钾盐在25–70°发生乙烯基环丁烷重排，为合成3-环己烯醇衍生物提供了一种有效的方法。2-乙烯基环丁酮是通过Trost的方法，通过烯烃和乙烯基烯酮的[2 + 2] -环加成反应，由α，β-不饱和羰基化合物制得的。然后加入氢化物或烷基锂试剂，生成2-乙烯基环丁醇盐，其可直接重排得到3-环己醇。这两种方法构成6元碳环的新[3 + 3]-和[4 + 2]环行方法。

  DOI：

  10.1016/s0040-4020(01)93268-5

文献信息

• NOVEL 3-(4(BENZYLOXY)PHENYL)HEX-4-INOIC ACID DERIVATIVE, METHOD OF PREPARING SAME AND PHARMACEUTICAL COMPOSITION FOR PREVENTING AND TREATING METABOLIC DISEASE INCLUDING SAME AS EFFECTIVE INGREDIENT
  申请人：HYUNDAI PHARM CO., LTD

  公开号：US20160024063A1

  公开（公告）日：2016-01-28

  The present invention relates to a novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, a preparation method thereof, and a pharmaceutical composition comprising the same as an active ingredient for the prevention and treatment of metabolic disease. The novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of the present invention has excellent activities of activating GPR40 protein and promoting insulin secretion accordingly but has no toxicity when co-administered with other drugs. That is, the novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of the present invention can be co-administered with other drugs and can promote the activation of GPR40 protein significantly, so that the composition comprising the same as an active ingredient can be efficiently used as a pharmaceutical composition for the prevention and treatment of metabolic disease such as obesity, type I diabetes, type II diabetes, incompatible glucose tolerance, insulin resistance, hyperglycemia, hyperlipidemia, hypertriglyceridemia, hypercholesterolemia, dyslipidemia, and syndrome X, etc.

  本发明涉及一种新型的3-(4-(苄氧基)苯基)己-4-羧酸衍生物，其制备方法以及包含该衍生物作为活性成分的药物组合物，用于预防和治疗代谢性疾病。本发明的这种新型的3-(4-(苄氧基)苯基)己-4-羧酸衍生物、其光学异构体或其药用可接受盐，对于激活GPR40蛋白并相应地促进胰岛素分泌具有优良活性，且在与其他药物联合使用时没有毒性。也就是说，本发明的这种新型的3-(4-(苄氧基)苯基)己-4-羧酸衍生物、其光学异构体或其药用可接受盐，可以与其他药物联合使用，并且能显著促进GPR40蛋白的激活，使得包含其作为活性成分的组合物能有效地用作预防和治疗诸如肥胖、I型糖尿病、II型糖尿病、糖耐量异常、胰岛素抵抗、高血糖、高脂血症、高甘油三酯血症、高胆固醇血症、血脂异常和X综合症等代谢性疾病的药物组合物。
• Syntheses with organoboranes. IX. Vinyl- and 1-alkenyldichloroboranes as ethylene and 1-alkene equivalents for the Diels–Alder reaction
  作者：Marek Zaidlewicz、Jacek R Binkul、Wojciech Sokół

  DOI：10.1016/s0022-328x(98)01175-9

  日期：1999.5

  Vinyl- and 1-alkenyldichloroboranes were used as dienophiles for the Diels–Alder reaction with representative aliphatic and cyclic 1,3-dienes. The organoborane adducts were transformed into the corresponding olefins either by protonolysis or by oxidation–mesylation–reduction. Direct protonolysis of the adducts gave in most cases mixtures of olefins whereas the reduction of mesylates with lithium triethylborohydride

  乙烯基和1-烯基二氯硼烷被用作与亲脂性和环状1,3-二烯代表的狄尔斯-阿尔德反应的亲二烯体。有机硼烷加合物通过质子分解或氧化-甲磺酰化-还原转化为相应的烯烃。在大多数情况下，加合物的直接质子分解得到烯烃的混合物，而用三乙基硼氢化锂还原甲磺酸酯则可得到高纯度的纯烯烃。
• Stereoselective [4+2]‐Cycloaddition with Chiral Alkenylboranes
  作者：Dongshun Ni、Brittany P. Witherspoon、Hong Zhang、Chen Zhou、K. N. Houk、M. Kevin Brown

  DOI：10.1002/anie.202000652

  日期：2020.7.6

  A method for the stereoselective [4+2]‐cycloaddition of alkenylboranes and dienes is presented. This transformation was accomplished through the introduction of a new strategy that involves the use of chiral N‐protonated alkenyl oxazaborolidines as dieneophiles. The reaction leads to the formation of products that can be readily derivatized to more complex structural motifs through stereospecific transformations

  提出了一种方法用于烯基硼烷和二烯的立体选择[4 + 2]-环加成反应。这种转化是通过引入一种新策略完成的，该策略涉及使用手性N质子化的烯基恶唑硼烷作为二烯亲和体。该反应导致形成产物，该产物可以通过C-B键的立体定向转化（例如氧化和同源化）而容易地衍生为更复杂的结构图案。反应的详细计算评估发现反离子对立体选择性的惊人作用。
• Alkylhalovinylboranes: a new class of Diels–Alder dienophiles
  作者：Pablo L. Pisano、Silvina C. Pellegrinet

  DOI：10.1039/c8ra07089j

  日期：——

  The Diels–Alder reactions of alkylhalovinylboranes have been investigated theoretically and experimentally. Alkylhalovinylboranes presented higher reactivity than the corresponding dialkylvinylboranes. Although endo/exo selectivities were high for the reactions with cyclopentadiene, facial selectivities for the chiral analogues were low. Our results demonstrate that the replacement of an alkyl group

  烷基卤乙烯基硼烷的 Diels-Alder 反应已在理论上和实验上进行了研究。烷基卤代乙烯基硼烷比相应的二烷基乙烯基硼烷具有更高的反应性。尽管与环戊二烯反应的内/外选择性很高，但手性类似物的面部选择性却很低。我们的结果表明，硼原子上的烷基被卤素取代会显着增加亲二烯性。
• COOLING SENSATION AGENT COMPOSITION, SENSORY STIMULATION AGENT COMPOSITION AND USE OF THE SAME
  申请人：Komatsuki Yasuhiro

  公开号：US20110081393A1

  公开（公告）日：2011-04-07

  Disclosed is a cooling sensation agent composition or sensory stimulation agent composition which contains at least one of diester compounds of dicarboxylic acid represented by the formula (1) wherein A represents CH 2 or CH═CH, n represents an integer of 0 to 4 when A is CH 2 , or 1 when A is CH═CH, B is an alcohol residue having 10 to 18 carbon atoms and containing a para-menthane skeleton, which may have a substituent, and C is an alcohol residue having 6 to 18 carbon atoms, which may have a substituent as well as a flavor or fragrance composition, a beverage, a food product, a perfume or cosmetic product, a toiletry product, daily utensil products or groceries, a fiber, a fiber product, clothes, clothing or a medicine, wherein the cooling sensation agent composition or the sensory stimulation agent composition is compounded.

  本文披露了一种包含以下化学式（1）所代表的二羧酸双酯化合物之一的冷却感剂组合物或感官刺激剂组合物，其中A代表CH2或CH═CH，n代表整数0至4（当A为CH2时）或1（当A为CH═CH时），B是含有10至18个碳原子并含有对蒎烷骨架的醇残基，可能有取代基，C是含有6至18个碳原子的醇残基，可能也有取代基，以及香料或香精组合物、饮料、食品产品、香水或化妆品产品、洗涤用品、日用品或杂货、纤维、纤维制品、衣服、服装或药品，其中复合了冷却感剂组合物或感官刺激剂组合物。