(S)-(-)-methyl 3-methylheptanoate | 99439-79-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-(-)-methyl 3-methylheptanoate
• 英文别名: (S)-methyl 3-methylheptanoate；(S)-3-methyl-heptanoic acid methyl ester；(S)-3-Methyl-heptansaeure-methylester；(3S)-3-Methyl-methylester Heptanoic Acid；methyl (3S)-3-methylheptanoate
• CAS: 99439-79-9
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: GZLDPMXJNRMXQC-QMMMGPOBSA-N

物化性质

• 沸点：
  176.5±8.0 °C(Predicted)
• 密度：
  0.874±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (S)-(-)-methyl 3-methylheptanoate 在 草酰氯 、 苯 作用下， 生成 (S)-3-methyl-heptanoic acid amide
  参考文献：
  名称：

  Staellberg; Stenhagen, Arkiv foer Kemi, 1950, vol. 2, p. 95,102

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R)-hexan-2-ol 在 水 、 三甲胺盐酸盐 、 sodium hydride 、 三乙胺 、 lithium chloride 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 (S)-(-)-methyl 3-methylheptanoate
  参考文献：
  名称：

  Stereospecific inversion of secondary tosylates to yield chiral methyl-branched building blocks, applied to the asymmetric synthesis of leafminer sex pheromones

  摘要：

  All four of the possible stereoisomers of 5,9-dimethylheptadecane, the major sex pheromone component secreted by female moths of the mountain-ash bentwing (Leucoptera scitella), were synthesized by the coupling of two chiral blocks with a methyl branch at the 2- or 3-position. The blocks were prepared by applying the stereospecific inversion of secondary tosylates, which were derived from (R)- and (S)-propylene oxide, and their enantiopurities were confirmed by chiral HPLC analysis. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.023

文献信息

• Highly Efficient Copper(I) Iodide-Tolyl-BINAP-Catalyzed Asymmetric Conjugate Addition of Methylmagnesium Bromide to α,β-Unsaturated Esters
  作者：Shun-Yi Wang、Tze-Keong Lum、Shun-Jun Ji、Teck-Peng Loh

  DOI：10.1002/adsc.200700567

  日期：2008.3.25

  A highly efficient asymmetric conjugate addition of methylmagnesium bromide (MeMgBr) to α,β-unsaturated esters catalyzed by copper(I) iodide-tolyl-BNIP (CuI-Tol-BINAP) is described.

  描述了由碘化铜（I）-甲苯基-BNIP（CuI-Tol-BINAP）催化的甲基溴化镁（MeMgBr）的高效不对称共轭加成反应。
• A General Strategy for the Introduction of Stereogenic Centers Bearing a Methyl Group: Total Synthesis of Sex Pheromones
  作者：Shun-Yi Wang、Ping Song、Yen-Jin Chin、Teck-Peng Loh

  DOI：10.1002/asia.201000663

  日期：2011.2.1

  We're bringing sexy back: The highly efficient introduction of stereogenic centers bearing methyl group by conjugate addition of RMgBr to α,β‐unsaturated esters has been employed in the total syntheses of two sex pheromones (see scheme). Binap=[1,1′‐binaphthalene]‐2,2′‐diylbis(diphenylphosphane).

  我们正带回性感：通过将RMgBr共轭加到α，β-不饱和酯中来高效引入带有甲基的立体异构中心已被用于两个性信息素的总合成中（参见方案）。Binap = [1,1'-联萘] -2,2'-二基双（二苯基膦）。
• Asymmetric conjugate addition of organometallic reagents to chiral vinyl sulfoximines
  作者：Stephen G. Pyne

  DOI：10.1021/jo00351a017

  日期：1986.1
• Copper‐Catalyzed Enantioselective Conjugate Addition of Grignard Reagents to α,β‐Unsaturated Esters
  作者：Fernando López、Syuzanna R. Harutyunyan、Auke Meetsma、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1002/anie.200500317

  日期：2005.4.29
• PYNE, ST. G., J. ORG. CHEM., 1986, 51, N 1, 81-87
  作者：PYNE, ST. G.

  DOI：——

  日期：——