methyl (1S,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate | 26770-96-7

• 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: methyl (1S,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
• 英文别名: methyl (1S)-trans-chrysanthemate；Methyl (-)-trans-Chrysanthemate；methyl chrysanthemate；trans-Chrysanthemummonocarbonsaeuremethylester；1-trans-Chrysantemumcarbonsaeuremethylester；trans-Chrysanthemumsaeuremethylester；Methyl chrysanthemate, trans-(-)-；methyl (1S,3S)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• CAS: 26770-96-7
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: ITNHSNMLIFFVQC-DTWKUNHWSA-N

物化性质

• 沸点：
  205.2±29.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  methyl (1S,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate 生成 (1S,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylic acid methyl ester
  参考文献：
  名称：

  CHEN, LIANG, XUADUN SHIFAN DASYUEH SYUEHBAO,(1989) N, S. 51-65

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-6-methyl-carvone 在 盐酸 、 sodium hydroxide 、 正丁基锂 、 硫酸 、 双氧水 、 lithium perchlorate 、 magnesium 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 27.41h， 生成 methyl (1S,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
  参考文献：
  名称：

  Electrooxidative cleavage of carbon-carbon bonds. 2. Double cleavage of .alpha.,.beta.-epoxy alkanones and enantiospecific syntheses of chiral methyl trans- and cis-chrysanthemates from (+)- and (-)-carvones

  摘要：

  DOI：

  10.1021/jo00160a002

文献信息

• Lewis Acid Catalyzed Enantioselective Photochemical Rearrangements on the Singlet Potential Energy Surface
  作者：Malte Leverenz、Christian Merten、Andreas Dreuw、Thorsten Bach

  DOI：10.1021/jacs.9b12068

  日期：2019.12.26

  The oxadi-π-methane rearrangement of 2,4-cyclohexadienones to bicyclic ketones was found to proceed with high enantioselectivity (92–97% ee) in the presence of catalytic amounts of a chiral Lewis acid (15 examples, 52–80% yield). A notable feature of the transformation is the fact that it proceeds on the singlet hypersurface and that no triplet intermediates are involved. Rapid racemic background reactions

  发现在催化量的手性路易斯酸（15 个例子，52-80% 产率）存在下，2,4-环己二烯酮的 oxadi-π-甲烷重排以高对映选择性（92-97% ee）进行）。转换的一个显着特征是它在单线态超曲面上进行并且不涉及三线态中间体。因此避免了快速的外消旋背景反应，并且催化剂负载可以保持低（10 mol%）。计算研究表明，通过锥形交叉点在路易斯酸结合的单线态中间体中确定对映选择性。该方法的实用性通过天然产物反菊酸的简洁合成得到了证明。
• Reactions of Vinylcyclopropane Epoxides with Samarium and Phosphorus Iodides
  作者：Alain Krief、Willy Dumont、Diane Baillieul

  DOI：10.1055/s-2005-917091

  日期：——

  Samarium diiodide on one hand, diphosphorus tetra-iodide, and phosphorus triiodide on the other, react with vinylcyclopropane epoxides to produce either allylic alcohols or vinylcyclopropanes resulting from cyclopropane ring-opening or deoxygenation of the epoxide, respectively.

  一方面，二碘化钐、四碘化二磷和另一方面的三碘化磷与乙烯基环丙烷环氧化物反应，分别由环丙烷开环或环氧化物脱氧产生烯丙醇或乙烯基环丙烷。
• METHOD FOR PRODUCING ORGANIC COMPOUND AND ORGANIC COMPOUND OBTAINED BY THE METHOD
  申请人：Enomura Masakazu

  公开号：US20110178199A1

  公开（公告）日：2011-07-21

  Disclosed herein are a reaction method and a production method of an organic compound which are capable of achieving high reaction selectivity according to the purpose and a high production rate of a target substance. The methods include at least two fluids, wherein at least one kind of the fluids is a fluid containing at least one organic compound and at least one kind of the fluids other than the above fluid is a fluid containing at least one reactant in the form of a liquid or solution, and the respective fluids join together in a thin film fluid foamed between processing surfaces arranged to be opposite to each other so as to be able to approach to and separate from each other, at least one of which rotates relative to the other, whereby an organic reaction is performed in the thin film fluid.

  本文公开了一种有机化合物的反应方法和生产方法，能够根据目的实现高反应选择性和目标物质的高产率。该方法包括至少两种流体，其中至少一种流体是含有至少一种有机化合物的流体，除上述流体外的至少一种流体是以液态或溶液形式含有至少一种反应物的流体。这些各自的流体在处理表面之间形成一个薄膜流体泡沫，这些处理表面相对排列以便能够相互接近和分离，其中至少有一个表面相对于另一个表面旋转，从而在薄膜流体中进行有机反应。
• A process for producing 3,3-dimethyl-2-formylcyclopropane-carboxylic acid ester
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1120393A1

  公开（公告）日：2001-08-01

  There is provided a process for producing 3,3-dimethyl-2-formylcyclopropanecarboxylic ester of formula (1): wherein R represents an alkyl group, a cycloalkyl group or an optionally substituted aralkyl group,    which comprises reacting chrysanthemic acid ester of formula (2): wherein R represents the same meaning as that described above, with hydrogen peroxide in the presence of at least one catalyst selected from tungstic oxide, tungstic acid, tugstate, alkylrhenium trioxide, molybdic oxide, molybdate, a heteropoly acid comprising a hetero atom selected from a phosphorus, boron or silicone atom and a poly atom selected from tungsten or molybdenum and a salt of said heteropoly acid.

  提供了一种生产式 (1) 的 3,3-二甲基-2-甲酰基环丙烷羧酸酯的工艺： 其中 R 代表烷基、环烷基或任选取代的芳烷基、 其中 R 代表烷基、环烷基或任选取代的芳烷基： 其中 R 代表与上述相同的含义，在至少一种选自氧化钨、钨酸、钨酸盐、烷基三氧化 铼、氧化钼、钼酸盐、杂多酸的催化剂存在下，与过氧化氢反应，杂多酸包含选自磷、 硼或硅原子的杂原子和选自钨或钼的多原子，以及所述杂多酸的盐。
• PROCESS FOR PRODUCING ORGANIC COMPOUND AND ORGANIC COMPOUND OBTAINED BY THE SAME
  申请人：M Technique Co., Ltd.

  公开号：EP2216312A1

  公开（公告）日：2010-08-11

  Disclosed herein are a reaction method and a production method of an organic compound which are capable of achieving high reaction selectivity according to the purpose and a high production rate of a target substance. The methods include at least two fluids, wherein at least one kind of the fluids is a fluid containing at least one organic compound and at least one kind of the fluids other than the above fluid is a fluid containing at least one reactant in the form of a liquid or solution, and the respective fluids join together in a thin film fluid formed between processing surfaces arranged to be opposite to each other so as to be able to approach to and separate from each other, at least one of which rotates relative to the other, whereby an organic reaction is performed in the thin film fluid.

  本文公开了一种有机化合物的反应方法和生产方法，该方法能够根据目的实现高反应选择性和目标物质的高生产率。这些方法包括至少两种流体，其中至少一种流体是含有至少一种有机化合物的流体，而除上述流体之外的至少一种流体是含有至少一种液体或溶液形式的反应物的流体，各自的流体以薄膜流体的形式结合在一起，薄膜流体形成于彼此相对的加工表面之间，以便能够相互接近和分离，其中至少一个加工表面相对于另一个加工表面旋转，从而在薄膜流体中进行有机反应。