(R)-(+)-methyl 2-hydroxy-4-methyl-4-pentenoate | 119072-56-9

• 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: (R)-(+)-methyl 2-hydroxy-4-methyl-4-pentenoate
• 英文别名: methyl 2-hydroxy-4-methyl-4-pentenoate；methyl (R)-2-hydroxy-4-methyl-4-pentenoate；methyl (2R)-2-hydroxy-4-methylpent-4-enoate
• CAS: 119072-56-9
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: UWXHOUJYXCMJSD-ZCFIWIBFSA-N

物化性质

• 沸点：
  190.8±20.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-methyl 2-hydroxy-4-methyl-4-pentenoate 生成 (R)-2-羟基-4-甲基戊酸
  参考文献：
  名称：

  MIKAMI, KOICHI;TERADA, MASAHIRO;NAKAI, TAKESHI;SAYO, NOBORU;KUMOBAYASHI, +

  摘要：

  DOI：
• 作为产物：
  描述：

  乙醛酸甲酯 、 异丁烯 在 二异丙氧基二氯化钛 、 (R)-1,1'-Bi-2-naphthol 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 8.0h， 以72%的产率得到(R)-(+)-methyl 2-hydroxy-4-methyl-4-pentenoate
  参考文献：
  名称：

  ASYMMETRIC CATALYTIC GLYOXYLATE-ENE REACTION: METHYL (2R)-2-HYDROXY-4-PHENYL-4-PENTENOATE

  摘要：

  DOI：

  10.15227/orgsyn.071.0014

文献信息

• Process for producing optically active alpha-hydroxycarboxylates
  申请人：Takasago International Corporation

  公开号：US04965398A1

  公开（公告）日：1990-10-23

  A process for preparing an .alpha.-hydroxycarboxylate represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents a lower alkyl group, a phenyl group or a cycloalkyl group, or R.sup.1 and R.sup.2 are bonded to each other to form a five- to seven-membered cycloalkenyl or bicycloalkenyl ring which may be substituted with a lower alkyl group; and R.sup.3 represents a lower alkyl group, which comprises reacting an olefin compound represented by formula (II): ##STR2## wherein R.sup.1 ' represents a hydrogen atom or a lower alkyl group; and R.sup.2 ' represents a lower alkyl group, a phenyl group or a cycloalkyl group, or R.sup.1 ' and R.sup.2 ' are bonded to each other to form a five- to seven-membered cycloalkyl or bicycloalkyl ring which may be substituted with a lower alkyl group, with a glyoxylate represented by formula (III): ##STR3## wherein R.sup.3 is as defined above, in the presence of a binaphthol-titanium complex represented by formula (IV): ##STR4## wherein X represents a chlorine atom or bromine atom.

  一种制备公式（I）所表示的α-羟基羧酸的方法：其中R1代表氢原子或低碳基；R2代表低碳基、苯基或环烷基，或R1和R2相互连接形成可以用低碳基取代的五至七元环烯基或双环烯基环；R3代表低碳基，包括将公式（II）所表示的烯烃化合物与公式（III）所表示的乙酰乙酸盐在公式（IV）所表示的联苯二酚钛配合物存在下反应：其中R1'代表氢原子或低碳基；R2'代表低碳基、苯基或环烷基，或R1'和R2'相互连接形成可以用低碳基取代的五至七元环烷基或双环烷基环；R3如上定义，在X代表氯原子或溴原子的联苯二酚钛配合物存在下进行。
• Enantioselective [2,3]-Wittig Rearrangement of Carboxylic Acid Derived Enolates by Tetradentate Chiral Lithium Amide
  作者：Ryuichi Shirai、Kenji Yatsuzuka、Midori Kawasaki

  DOI：10.1055/a-2039-6352

  日期：——

  A chiral lithium amide mediated enantioselective [2,3]-Wittig rearrangement of carboxylic acid enolate has been developed. The reaction proceeds through the formation of a chiral mixed aggregate that shields one enantioface of enolate anion to give a highly functionalized chiral α-hydroxycarboxylic acid.

  摘要 开发了一种手性锂酰胺介导的羧酸对映体选择性 [2,3]-Wittig 重排反应。该反应通过形成手性混合聚集体来屏蔽烯酸根阴离子的一个对映面，从而得到高度官能化的手性α-羟基羧酸。
• Mikami, Koichi; Terada, Masahiro; Nakai, Takeshi, Journal of the American Chemical Society, 1990, vol. 112, # 10, p. 3949 - 3954
  作者：Mikami, Koichi、Terada, Masahiro、Nakai, Takeshi

  DOI：——

  日期：——
• Asymmetric glyoxylate-ene reaction catalyzed by chiral titanium complexes: a practical access to .alpha.-hydroxy esters in high enantiomeric purities
  作者：Koichi Mikami、Masahiro Terada、Takeshi Nakai

  DOI：10.1021/ja00187a093

  日期：1989.3
• Ene approach to asymmetric catalysis of the “Sakurai-Hosomi reaction”, Lewis acid-promoted carbonyl-addition reaction with allylic silanes
  作者：Koichi Mikami、Satoru Matsukawa

  DOI：10.1016/s0040-4039(00)76849-3

  日期：1994.5

  The chiral Lewis acid prepared from (R)-binaphthol and diisopropoxytitanium dichloride catalyzes the reaction of glyoxylate esters with methallylsilanes to afford mainly ene-type products rather than the products expected from the ''usual'' Sakurai-Hosomi reaction. The ene-type products lead eventually after protodesilylation to the ''usual'' products with high enantiomeric excesses.