(2E,1'S,2'R,5'S)-but-2-enedioic acid bis(2'-isopropyl-5'methyl-cyclohexyl) ester | 86287-64-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2E,1'S,2'R,5'S)-but-2-enedioic acid bis(2'-isopropyl-5'methyl-cyclohexyl) ester
• 英文别名: (E)-1,4-bis((1S,2R,5S)-2-isopropyl-5-methylcarbcyclohex-1-oxy)but-2-ene；bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) fumarate；fumaric acid di-(+)-menthyl ester；fumaric acid (+)-menthol diester；(1S,3S,4R)-dimenthyl fumarate；di-(+)-menthyl fumarate；bis[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] (E)-but-2-enedioate
• CAS: 86287-64-1
• 化学式: C₂₄H₄₀O₄
• 分子量: 392.579
• InChiKey: HTJZKHLYRXPLLS-ZFVXUVLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E,1'S,2'R,5'S)-but-2-enedioic acid bis(2'-isopropyl-5'methyl-cyclohexyl) ester 在 氯化二乙基铝 、 三乙胺 、 二异丙胺 、 间氯过氧苯甲酸 作用下， 以 正己烷 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 62.67h， 生成 (1R,2R,3Z,5R,1'S,2'R,5'S)-5-methanesulfonyloxy-cyclohex-3-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester
  参考文献：
  名称：

  Total synthesis of the polyenoyltetramic acid polycephalin C

  摘要：

  The total synthesis of the polyenoyltetramic acid polycephalin C is described. Key steps of the synthesis include a double Swern oxidation, double Takai reaction and a double Stille reaction. In addition, the absolute stereochemistry of the ring junction has been determined by synthesis of both isomers and comparison of their CD spectra with natural polycephalin C. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00816-0
• 作为产物：
  描述：

  D-薄荷醇 在 吗啉 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 27.0h， 生成 (2E,1'S,2'R,5'S)-but-2-enedioic acid bis(2'-isopropyl-5'methyl-cyclohexyl) ester
  参考文献：
  名称：

  Total synthesis of the polyenoyltetramic acid polycephalin C

  摘要：

  The total synthesis of the polyenoyltetramic acid polycephalin C is described. Key steps of the synthesis include a double Swern oxidation, double Takai reaction and a double Stille reaction. In addition, the absolute stereochemistry of the ring junction has been determined by synthesis of both isomers and comparison of their CD spectra with natural polycephalin C. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00816-0

文献信息

• USE OF COMPOSITIONS OBTAINED BY CALCINING PARTICULAR METAL-ACCUMULATING PLANTS FOR IMPLEMENTING CATALYTICAL REACTIONS
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US20150376224A1

  公开（公告）日：2015-12-31

  The use of metal-accumulating plants for implementing chemical reactions especially catalytical reactions.

  金属积累植物用于实现化学反应，特别是催化反应的使用。
• Enantioselective total synthesis of bilobalide, A C15 ginkgolide
  作者：E.J. Corey、Wei-guo Su

  DOI：10.1016/0040-4039(88)85179-7

  日期：1988.1

  An enantioselective total synthesis of bilobalide 1 has been effected from diester 5 using stereospecific conversion to 7 via intermediate 6.

  白果内酯的对映体选择性全合成1已经从二酯进行5使用立体有择转化为7经由中间体6。
• Asymmetric Synthesis of a New Salen Type-titanium Complex as the Catalyst for Asymmetric Trimethylsilylcyanation of Aldehydes
  作者：Zheng-Chang Lin、Chinpiao Chen

  DOI：10.1002/jccs.201000101

  日期：2010.8

  This work describes the asymmetric synthesis of a new salen‐type ligand via a Diels‐Alder reaction and Curtius rearrangement. The ligand with a norbornane skeleton was used in the trimethylsilylcyanation of aldehydes, but the enantioselectivity was 55%ee. The norborane skeleton was cleaved to destroy this rigidity, and the eanatioselectivity was thereby increased to 85%ee.

  这项工作描述了通过Diels-Alder反应和Curtius重排的新Salen型配体的不对称合成。具有降冰片烷骨架的配体用于醛的三甲基甲硅烷基氰化中，但对映选择性为55％ee。切割去甲硼烷骨架以破坏该刚性，从而将选择性选择性提高至85％ee。
• Use of metal-accumulating plants for implementing chemical reactions
  申请人：Grison Claude

  公开号：US09149796B2

  公开（公告）日：2015-10-06

  The use of metal-accumulating plants for implementing chemical reactions.

  利用富集金属的植物来实施化学反应。
• Semicorrin metal complexes as enantioselective catalysts. Part 2. Enantioselective cyclopropane formation from olefins with diazo compounds catalyzed by chiral (semicorrinato)copper complexes
  作者：Hugo Fritschi、Urs Leutenegger、Andreas Pfaltz

  DOI：10.1002/hlca.19880710621

  日期：1988.9.28

  were obtained (Table 2). Usually, the reactions were carried out using bis(semicorrinato)copper(II) complexes as precatalysts. In order to produce active catalysts, these complexes had to be activated first by heating in the presence of diazoacetate or by treatment with phenylhydrazine. Experiments with (semicorrinato)copper(I) complexes, prepared in situ from copper(I) tert-butoxide (Scheme 4), suggest

  发现手性，C 2对称半corrin配体的铜配合物是从烯烃与重氮化合物形成环丙烷的有效催化剂。在催化剂的1％模式下，重氮乙酸烷基酯与末端烯烃如苯乙烯，丁二烯和1-庚烯平稳地反应，得到相应的光学活性环丙烷羧酸衍生物（表1方案2）。使用其中一种催化剂，对映选择性高达97％ee （表2）。通常，该反应使用双（准corrinato）铜（II）配合物作为预催化剂进行。为了生产活性催化剂，必须首先通过在重氮乙酸酯存在下加热或通过苯肼处理来活化这些配合物。使用由叔丁醇铜（I）原位制备的（semicorrinato）铜（I）配合物进行的实验（方案4）表明，实际的催化剂是[单（semicorrinarinato）]铜（I）。