l-menthyl crotonate | 64838-58-0

• 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: l-menthyl crotonate
• 英文别名: l-menthyl 2-butenoate；menthyl crotonate；(-)-Menthylcrotonat；1-(1'R,2'S,5'R)-5'-methyl-2'-(1-methylethyl)cyclohexyl 2-butenoate；(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl but-2-enoate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] but-2-enoate
• CAS: 64838-58-0
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: DNVICYQGCINFSQ-FRRDWIJNSA-N

物化性质

• 沸点：
  280.0±9.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  l-menthyl crotonate 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 l-menthyl 4-bromocrotonate
  参考文献：
  名称：

  氧化苯乙烯与膦酸酯-碳负离子反应的机理

  摘要：

  将绝对构型分配给反式-2-苯基环丙烷-羧酸表明，旋光性氧化苯乙烯与膦酸酯-碳负离子之间的反应在不对称中心进行反演。

  DOI：

  10.1016/0040-4020(63)85011-5
• 作为产物：
  描述：

  L-薄荷醇 、 巴豆酰氯 在 N,N-二乙基苯胺 作用下， 以 Petroleum ether 为溶剂， 生成 l-menthyl crotonate
  参考文献：
  名称：

  氧化苯乙烯与膦酸酯-碳负离子反应的机理

  摘要：

  将绝对构型分配给反式-2-苯基环丙烷-羧酸表明，旋光性氧化苯乙烯与膦酸酯-碳负离子之间的反应在不对称中心进行反演。

  DOI：

  10.1016/0040-4020(63)85011-5

文献信息

• Hypervalent iodine(III) catalyzed radical hydroacylation of chiral alkylidenemalonates with aliphatic aldehydes under photolysis
  作者：Sermadurai Selvakumar、Qi-Kai Kang、Natarajan Arumugam、Abdulrahman I. Almansour、Raju Suresh Kumar、Keiji Maruoka

  DOI：10.1016/j.tet.2017.08.018

  日期：2017.10

  bearing (−)-8-phenylmenthol as a chiral auxiliary with aliphatic aldehydes is realized under photolysis. This work represent the first example of diastereoselective addition of acyl radicals to olefins to afford chiral ketones in a highly stereoselective fashion. The reaction is initiated by the photolysis of hypervalent iodine(III) catalyst under mild and metal-free conditions. The synthetic potential

  在光解作用下，实现了带有（-）-8-苯基薄荷醇作为手性助剂的亚烷基丙二酸酯的高价碘（III）催化的非对映选择性自由基加氢酰化。这项工作代表了将酰基非对映选择性加成至烯烃，从而以高度立体选择性的方式得到手性酮的第一个例子。该反应是通过在温和且不含金属的条件下光解高价碘（III）催化剂而引发的。该方法的合成潜力已通过（-）-亚甲基乳酸内酯的短时正式合成得到了证明。
• ASYMMETRIC INDUCTION IN FREE RADICAL ADDITION OF THIOLS TO<i>l</i>-MENTHYL CROTONATE
  作者：Masakuni Yoshihara、Hisashi Fujihara、Toshihisa Maeshima

  DOI：10.1246/cl.1980.195

  日期：1980.2.5

  Diastereoface differentiation of l-menthyl crotonate has been achieved in the radical addition with achiral thiols such as thiolacetic acid, mercaptoacetate, and mercaptoacetic acid.

  巴豆酸 l-薄荷酯的非对映体分化是通过与非手性硫醇（如硫羟乙酸、巯基乙酸盐和巯基乙酸）的自由基加成实现的。
• Diastereoselective Radical Hydroacylation of Alkylidenemalonates with Aliphatic Aldehydes Initiated by Photolysis of Hypervalent Iodine(III) Reagents
  作者：Sermadurai Selvakumar、Ryu Sakamoto、Keiji Maruoka

  DOI：10.1002/chem.201600425

  日期：2016.5.4

  Diastereoselective radical hydroacylation of chiral alkylidenemalonates with aliphatic aldehydes is realized by the combination of a hypervalent iodine(III) reagent and UV‐light irradiation. The reaction is initiated by the photolysis of hypervalent iodine(III) reagents under mild, metal‐free conditions, and is the first example of diastereoselective addition of acyl radicals to olefins to afford chiral

  手性亚烷基丙二酸酯与脂族醛的非对映选择性自由基加氢酰化是通过高价碘（III）试剂和紫外线照射的结合实现的。该反应是通过在温和，无金属的条件下对高价碘（III）试剂进行光解而引发的，并且是将自由基自由基非对映选择性地加成到烯烃上，从而以高度立体选择性的方式提供手性酮的第一个实例。所获得的旋光性酮是有用的手性合成子，以（-）-亚甲基半乳糖苷的短形式合成为例。
• Total synthesis of (+)-papulacandin D
  作者：Scott E. Denmark、Tetsuya Kobayashi、Christopher S. Regens

  DOI：10.1016/j.tet.2010.03.093

  日期：2010.6

  A total synthesis of (+)-papulacandin D has been achieved in 31 steps, in a 9.2% overall yield from commercially available materials. The synthetic strategy divided the molecule into two nearly equal sized subunits, the spirocyclic C-arylglycopyranoside and the polyunsaturated fatty acid side-chain. The C-arylglycopyranoside was prepared in 11 steps in a 30% overall yield from triacetoxyglucal. The fatty acid side-chain was also prepared in 11 steps in a 30% overall yield from geraniol. The key strategic transformations in the synthesis are: (1) a palladium-catalyzed, organosilanolate-based cross-coupling reaction of a dimethylglucal-silanol with an electron-rich and sterically hindered aromatic iodide and (2) a Lewis-base catalyzed, enantioselective allylation reaction of a dienal and allyltrichlorosilane. A critical element in the successful execution of the synthesis was the development of a suitable protecting group strategy that satisfied a number of stringent criteria. (C) 2010 Elsevier Ltd. All rights reserved.
• Menthyl 2-bromocrotonate and menthyl 4-bromocrotonate: reagents for chiral vinylogous Darzens and Reformatsky reactions
  作者：Tomas Hudlicky、Lilian Radesca、H. Lee Rigby

  DOI：10.1021/jo00228a049

  日期：1987.9