(1S,3S,4S) methyl 3-hydroxy-4-methoxy-1-cyclohexanecarboxylate | 139893-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3S,4S) methyl 3-hydroxy-4-methoxy-1-cyclohexanecarboxylate
• 英文别名: (1S,3S,4S)-methyl 3-hydroxy-4-methoxycyclohexanecarboxylate；methyl (1S,3S,4S)-3-hydroxy-4-methoxycyclohexane-1-carboxylate
• CAS: 139893-84-8
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: PWYYTGMWYVWTGC-FXQIFTODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3S,4S) methyl 3-hydroxy-4-methoxy-1-cyclohexanecarboxylate 在 hydroxide 作用下， 生成 (1R,3R,4R)-3-hydroxy-4-methoxycyclohexane-1-carboxylic acid
  参考文献：
  名称：

  Regiochemical control of the ring-opening of 1,2-epoxides by means of chelating processes. 2. Synthesis and reactions of the cis- and trans-oxides of 4-[(benzyloxy)methyl]cyclohexene, 3-cyclohexenemethanol, and methyl 3-cyclohexenecarboxylate

  摘要：

  The synthesis of the diastereoisomeric epoxides cis-1b-d and trans-2b-d and the products of their ring-opening by various nucleophiles are described. The results of the ring-openings of the trans-epoxides 2b-d can be rationalized by combining stereoelectronic and conformational arguments. However, the regioselectivity of the ring-openings of the cis-epoxides 1b-d can, in principle, be influenced by the chelation of a metal ion by the oxygen atom of the epoxy group and that of the substituent on the 4-position. The results of the reactions of the cis-epoxides 1b-d indicate that, to some degree, chelation is indeed a factor. How important a factor it is is dependent both on the reaction conditions and on the concentration and nature of the metal ion. In the ring-openings of the cis-epoxides 1b and 1d, chelation seems to be a larger factor than it is in the ring-openings of cis-epoxide 1c. However, in no case is chelation as large a factor as it was in the ring-openings of the cis-epoxide 1a, which was studied earlier. On the other hand, the autocatalyzed methanolysis, under neutral conditions, of epoxy acid 1e, followed by CH2N2 methylation of the crude product, afforded a mixture of the two regioisomeric hydroxy ethers in which the C-2-type compound predominates. This result suggests that intramolecular hydrogen bonding may determine the reactive conformation of 1e.

  DOI：

  10.1021/jo00031a018
• 作为产物：
  描述：

  依度沙班杂质80 在 sodium hydroxide 、 硫酸 作用下， 以 异丙醇 为溶剂， 反应 4.0h， 生成 (1S,3S,4S) methyl 3-hydroxy-4-methoxy-1-cyclohexanecarboxylate
  参考文献：
  名称：

  通过（S）-（-）-3-环己烯羧酸实际，不对称合成免疫抑制剂FK-506的环己基C 28 -C 34片段

  摘要：

  报道了FK-506的环己基片段的不对称合成。这种新的合成方法（五个步骤，总产率为30％）首次从（S）-（-）-3-环己烯羧酸（S- 2）代替常用的R形式（酸R- 2）开始并利用差向异构反应。通过回收来自差向异构化步骤的回收的起始产物（羟基酯7c），将总产率提高到35％。

  DOI：

  10.1016/s0040-4020(01)89015-3

文献信息

• NITROOXY CYCLOALKANE DERIVATIVES
  申请人：Ali Amjad

  公开号：US20110230532A1

  公开（公告）日：2011-09-22

  A compound having the structure wherein Y is selected from the group consisting of —C(O)OR 2 , —C(O)NHR 8 , —C(CH 2 ) 1-2 OR3, OH, and or a pharmaceutically acceptable salt thereof, and methods of using the compounds for treating hypertension.

  一种具有以下结构的化合物，其中Y是从以下群组中选择的：—C(O)OR2、—C(O)NHR8、—C(CH2)1-2OR3、OH，或其药学上可接受的盐，以及使用该化合物治疗高血压的方法。
• US8530521B2
  申请人：——

  公开号：US8530521B2

  公开（公告）日：2013-09-10