3-((1S,2R)-1,2-Dimethyl-6-oxo-cyclohexyl)-propionic acid methyl ester | 234077-99-7

• 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: 3-((1S,2R)-1,2-Dimethyl-6-oxo-cyclohexyl)-propionic acid methyl ester
• 英文别名: methyl 3-[(1S,2R)-1,2-dimethyl-6-oxocyclohexyl]propanoate
• CAS: 234077-99-7
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: LYBYZLQMMZFTAR-SKDRFNHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((1S,2R)-1,2-Dimethyl-6-oxo-cyclohexyl)-propionic acid methyl ester 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S,3R)-2-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,3-dimethyl-cyclohexanol
  参考文献：
  名称：

  卤氧平的全合成及结构修饰

  摘要：

  卤氧杂环己烷的首次全合成是通过 1,4 加成在 C10 处构建四级中心和卤代醚化在 C7 处生成叔醚来完成的。通过组装不同的对映体结构单元并改变 C10 和 C15 之间的相对构型，确定了卤氧杂平的正确结构。

  DOI：

  10.1002/chem.202004847
• 作为产物：
  描述：

  2,3-dimethylcyclohexanone 在 对甲苯磺酸 、 对苯二酚 作用下， 以 苯 为溶剂， 反应 95.0h， 生成 3-((1S,2R)-1,2-Dimethyl-6-oxo-cyclohexyl)-propionic acid methyl ester
  参考文献：
  名称：

  卤氧平的全合成及结构修饰

  摘要：

  卤氧杂环己烷的首次全合成是通过 1,4 加成在 C10 处构建四级中心和卤代醚化在 C7 处生成叔醚来完成的。通过组装不同的对映体结构单元并改变 C10 和 C15 之间的相对构型，确定了卤氧杂平的正确结构。

  DOI：

  10.1002/chem.202004847

文献信息

• Isolation and Structure of Striatenic Acid from Liverwort Cheilolejeunea serpentina and the Absolute Configuration by Synthesis
  作者：Motoo Tori、Akihito Aiba、Hiroki Koyama、Toshihiro Hashimoto、Katsuyuki Nakashima、Masakazu Sono、Yoshinori Asakawa

  DOI：10.1016/s0040-4020(00)00069-7

  日期：2000.3

  Striatenic acid has been isolated from the liverwort Cheilolejeunea serpentina collected in Malaysia and its structure was determined on the basis of extensive 2D NMR techniques. The absolute configuration was established by synthesis of the optically active methyl ester.

  已从马来西亚收集的地艾草蛇形草中分离出三酸。其结构是根据广泛的2D NMR技术确定的。绝对构型是通过合成光学活性的甲酯来建立的。
• Total synthesis of optically active liverwort sesquiterpenes, trifarienols A and B, using phenylethylamine as a chiral auxiliary
  作者：Motoo Tori、Kenji Hisazumi、Tomonari Wada、Masakazu Sono、Katsuyuki Nakashima

  DOI：10.1016/s0957-4166(99)00067-1

  日期：1999.3

  The imine of (rac)-2,3-dimethylcyclohexanone 10a with (S)-(-)-phenylethylamine was reacted with methyl acrylate to yield methyl (1'S,6'R)-3-(1',6'-dimethyl-2'-oxocyclohexyl)propanoate 4a in 26% (97% eel)after hydrolysis. When (2RS,3R)-2,3-dimethylcyclohexanone 10b, was used, the same product 4b was obtained in 59% yield (>99.5% ee) after hydrolysis. When (2RS,3R)-2,3-dimethylcyclohexanone 10b and (R)-(+)-phenylethylamine were used, the reaction underwent in only 5% yield, the products being 4c, 12, 13, 14, and 15. Thus, the reaction of 3b with methyl acrylate is a matched case, while that of 3c is a mismatched case. These phenomena are explained by the nonbonded interaction of methyl acrylate with chiral phenylethylamine and the methyl group at the 6'-position of the cyclohexanone ring in the transition state. The propanoate product 4b was successfully transformed into liverwort sesquiterpene (+)-trifarienol A 1 and (-)-trifarienol B 2 in 10 steps. We have developed an HPLC method to determine the ees of 2,2-disubstituted and 2,2,3-trisubstituted cyclohexanones using the corresponding pentafluorophenyl esters. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of a homochiral ketone having a pinguisane skeleton using phenylethylamine as a chiral auxiliary: a formal total synthesis of deoxopinguisone
  作者：Motoo Tori、Chiho Makino、Kenji Hisazumi、Masakazu Sono、Katsuyuki Nakashima

  DOI：10.1016/s0957-4166(01)00041-6

  日期：2001.2

  A homochiral bicyclic ketone having a pinguisane skeleton has: been synthesised starting from homochiral methyl 3-[(1 'S,6 'R)-1 ' ,6 ' -dimethyl-2 ' -oxo-1-yl]propionate prepared from pulegone using phenylethylamine as a chiral auxiliary. The five-membered ring was constructed by the Hosomi-Sakurai reaction of the allylsilane derived from the ketone. This synthesis can be considered a formal synthesis of deoxopinguisone. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Total Synthesis and Structure Revision of Halioxepine
  作者：Caroline Poock、Markus Kalesse

  DOI：10.1002/chem.202004847

  日期：2021.1.21

  total synthesis of halioxepine is accomplished using a 1,4‐addition for constructing the quaternary center at C10 and a halo etherification for the generation of the tertiary ether at C7. The correct structure of halioxepine was determined by assembling different enantiomeric building blocks and by changing the relative configuration between C10 and C15.

  卤氧杂环己烷的首次全合成是通过 1,4 加成在 C10 处构建四级中心和卤代醚化在 C7 处生成叔醚来完成的。通过组装不同的对映体结构单元并改变 C10 和 C15 之间的相对构型，确定了卤氧杂平的正确结构。