2-环己基琥珀酸二甲酯 | 40745-21-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-环己基琥珀酸二甲酯
• 英文名称: dimethyl 2-cyclohexylidenesuccinate
• 英文别名: Cyclohexylidenbernsteinsaeure-dimethylester；Dimethyl 2-cyclohexylidenebutanedioate
• CAS: 40745-21-9
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: VSBQGEGQOMLLHH-UHFFFAOYSA-N

物化性质

• 沸点：
  309.5±17.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2-环己基琥珀酸二甲酯 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 2-cyclohexylidene-1,4-bis(methylsulfonyloxy)butane
  参考文献：
  名称：

  Synthesis of (E)-3-Alkylidenepyrrolidines by Nucleophilic Ring Closure of (E)-2-Alkylidene-1,4-diol Derivatives

  摘要：

  DOI：

  10.1002/1099-0690(200008)2000:16<2927::aid-ejoc2927>3.3.co;2-p
• 作为产物：
  描述：

  丁二酸二甲酯 生成 2-环己基琥珀酸二甲酯
  参考文献：
  名称：

  Banerjee , S.; Bagavant, G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 5, p. 362 - 365

  摘要：

  DOI：

文献信息

• Bromine-Induced Facile Synthesis of Butenolides and Spirobutenolides from Sterically Congested Tetrasubstituted Dialkyl Alkylidene Succinates
  作者：Narshinha Argade、Ramesh Patel

  DOI：10.1055/s-0029-1219233

  日期：2010.4

  Starting from sterically congested tetrasubstituted dialkyl alkylidene succinates, facile general approach to several dialkyl substituted butenolides and spirobutenolides with the generation of quaternary carbon center has been demonstrated via bromine-induced dealkylative regioselective intramolecular cyclization and dehydrobromination pathway. The mechanistic aspects involved in the formation of butenolides have been also described in brief.

  从立体拥挤的四取代二烷基烯基琥珀酸酯出发，通过溴诱导的脱烷基化区域选择性分子内环化及脱溴化氢反应途径，已经证明了合成几种二烷基取代的丁烯内酯和螺丁烯内酯并生成四级碳中心的简便通用方法。对形成丁烯内酯的机理方面也进行了简要描述。
• Phase-Transfer-Catalyzed Asymmetric Annulations of Alkyl Dihalides with Oxindoles: Unified Access to Chiral Spirocarbocyclic Oxindoles
  作者：Min Gao、Yongyi Li、Xuemin Li、Lin Hu

  DOI：10.1021/acs.orglett.1c04174

  日期：2022.1.28

  A general phase-transfer-catalyzed asymmetric (n+1) (n = 4 or 5) annulation reaction, featuring the direct coupling of simple oxindoles with alkyl dihalides that are allylic/benzylic and non-allylic/benzylic, has been developed to provide previously inaccessible cyclopentane- and cyclohexane-fused spirooxindole scaffolds with high yields and enantioselectivities (88–95% ee). Along with a broad scope

  已开发出一种通用的相转移催化不对称 ( n +1) ( n = 4 或 5) 环化反应，其特点是简单的羟吲哚与烯丙基/苄基和非烯丙基/苄基的烷基二卤化物直接偶联，以提供以前无法获得的环戊烷和环己烷融合的螺氧吲哚支架具有高产率和对映选择性（88-95% ee）。除了广泛的范围和温和的条件外，新协议还可以对药物 ubrogepant 的核心进行两步和克级合成。
• Conjugate addition of nitroalkanes to dimethyl maleate. Regioselective formation of both monoesters of 2-alkylsuccinic acids
  作者：Roberto Ballini、Giovanna Bosica、Alessandro Palmieri、Marino Petrini、Claudio Pierantozzi

  DOI：10.1016/s0040-4020(03)01175-x

  日期：2003.9

  Diesters of (E)-2-alkylidenesuccinic acids obtained by conjugate addition of nitroalkanes to dimethyl maleate can be selectively monohydrolyzed at the more reactive carboxyl group to the corresponding half-ester. Alternatively, total hydrolysis to the diacid allows a subsequent selective methyl esterification of the alkanoic carboxyl group to give the other regioisomeric half-ester. 2-Alkylsuccinic

  通过将硝基烷烃共轭加成到马来酸二甲酯中而获得的（E）-2-亚烷基琥珀酸的二酯可以在反应性更高的羧基上选择性地单水解成相应的半酯。可选择地，全部水解为二酸允许链烷羧基的随后的选择性甲基酯化，以给出其他区域异构的半酯。可以通过不饱和衍生物的催化加氢最终获得2-烷基琥珀酸单酯。
• The Reaction of Propargyl Compounds with Carbon Monoxide and Water in the Presence of Iron Carbonyl Catalyst
  作者：Fumio Wada、Tsutomu Matsuda

  DOI：10.1246/bcsj.46.510

  日期：1973.2

  The faster rate of reaction and the product obtained were interpreted by a scheme involving a concerted attack of hydroirontetracarbonyl anion, HFe(CO)4−, at the terminal position to split off the group at C-3. The mononuclear hydrido anion was assumed to be an active catalytic species in the reaction on the basis of both the infrared spectra of the catalyst system under the reaction conditions and the

  在五羰基铁胺催化剂的存在下，炔丙醇及其乙酸酯和甲醚与一氧化碳和水在羟甲基化条件下的反应速度比1-丁炔-4-醇、1-戊炔-5-醇和烷基乙炔伴随消除C-3 处的官能团，得到甲基琥珀酸二甲酯。3-甲基-1-丁炔-3-醇和1-乙炔基环己醇以类似方式反应，但得到不饱和单酯和二酯、饱和和不饱和的混合物。更快的反应速率和获得的产物通过涉及氢铁四羰基阴离子HFe(CO)4-在末端位置的协同攻击以分裂C-3处的基团的方案来解释。
• Regio- and stereoselective selenium dioxide allylic oxidation of (E)-dialkyl alkylidenesuccinates to (Z)-allylic alcohols: Synthesis of natural and unnatural butenolides
  作者：Ramesh M. Patel、Vedavati G. Puranik、Narshinha P. Argade

  DOI：10.1039/c1ob05709j

  日期：——

  allylic alcohol formation of dialkyl alkylidenesuccinates has been demonstrated to accomplish one-step syntheses of several essential butenolides and fused butenolidesvia an unusual E- to Z- carbon–carbon double bond isomerisation followed by the lactonization pathway. The observed regio- and stereoselective SeO2 allylic oxidation protocol has also been extended to the diastereoselective total synthesis

  首次证明SeO 2诱导的二烷基亚烷基琥珀酸二烷基酯的（Z）选择性烯丙醇的形成通过不寻常的E-到Z-碳-碳双键异构化然后进行内酯化来完成几种基本丁烯内酯和稠合丁烯内酯的一步合成。途径。观察到的区域和立体选择性SeO 2烯丙基氧化方案也已扩展到生物活性天然产物异内酯的非对映选择性全合成，其直接转化为薄荷酸内酯和γ-内酯分子内重排为δ-内酯的例子。