(-)-methyl 2-hydroxy-4-phenyl-4-pentenoate | 119072-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (-)-methyl 2-hydroxy-4-phenyl-4-pentenoate
• 英文别名: methyl (R)-2-hydroxy-4-phenyl-4-pentenoate；methyl (2R)-2-hydroxy-4-phenylpent-4-enoate
• CAS: 119072-58-1
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: HCXDMVVQFJFXPO-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (-)-methyl 2-hydroxy-4-phenyl-4-pentenoate 、 碘甲烷 在 silver(l) oxide 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以110 mg的产率得到(R)-methyl 2-methoxy-4-phenyl-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
• 作为产物：
  描述：

  2-苯基-1-丙烯 以97%的产率得到
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Asymmetric catalysis by a new type of chiral binaphthol-titanium complex
  作者：Dai Kitamoto、Hironori Imma、Takeshi Nakai

  DOI：10.1016/0040-4039(95)00134-x

  日期：1995.3

  A new type of chiral 1,1′-bi-2-naphthol (BINOL)-derived titanium complex, prepared via complete hydrolysis of the complex formed in situ by mixing (i-PrO)4Ti and (R)-BINOL followed by azeotrope, serves as an efficient and moisture-tolerable enantioselective catalyst for the glyoxylate-ene reaction (>98% ee), and shows a remarkable level of asymmetric amplification therein. A μ-oxo dimer structure is

  一种新型的手性1,1'-联-2-萘酚（BINOL）衍生的钛配合物，通过将（i-PrO）4 Ti和（R）-BINOL混合后原位形成的配合物完全水解而制得共沸物，作为乙醛酸酯-烯反应（> 98％ee）的有效且耐湿的对映选择性催化剂，在其中显示出显着水平的不对称扩增。提出了一种用于新催化剂的μ-氧代二聚体结构。
• Remarkable positive nonlinear effect in the enantioselective glyoxylate–ene reaction catalysed by a chiral titanium complex
  作者：Masahiro Terada、Koichi Mikami、Takeshi Nakai

  DOI：10.1039/c39900001623

  日期：——

  The enantioselective glyoxylate–ene reaction catalysed by chiral titanium complex derived from partially resolved BINOL is found to exhibit a remarkable level of asymmetric amplification, wherein the optical yield of the product significantly exceeds the enantiomeric purity of the chiral auxiliary employed.

  发现由部分拆分的BINOL衍生的手性钛络合物催化的对映选择性乙醛酸酯-烯反应显示出显着水平的不对称扩增，其中产物的旋光收率大大超过了所用手性助剂的对映体纯度。
• Highly Enantioselective Carbonyl-ene Reactions Catalyzed by In(III)−PyBox Complex
  作者：Jun-Feng Zhao、Hoi-Yan Tsui、Pei-Jia Wu、Jun Lu、Teck-Peng Loh

  DOI：10.1021/ja807501a

  日期：2008.12.10

  A highly enantioselective carbonyl-ene reaction catalyzed by In(III)−pybox is described. Both 1,1-disubstituted alkenes and 1,1,2-trisubstituted alkenes proceeded smoothly to give the ene products in high yields up to 97% and with excellent diastereoselectivity and enantioselectivities up to >99:1 and 99%, respectively.

  描述了由 In(III)-pybox 催化的高度对映选择性羰基 - 烯反应。1,1-二取代烯烃和 1,1,2-三取代烯烃均能顺利进行，以高达 97% 的高产率得到 ene 产物，并且具有优异的非对映选择性和对映选择性分别高达 >99:1 和 99%。
• Binaphthol-derived titanium µ-oxo complex: a new type of asymmetric catalyst for carbonyl-ene reaction with glyoxylate
  作者：Masahiro Terada、Koichi Mikami

  DOI：10.1039/c39940000833

  日期：——

  The binaphthol (binol)-derived chiral titanium µ-oxo complex O is obtained accidentally upon toluene azetropy from a solution of binol and (PriO)2 TiCl2 after filtration of ms 4 Å and shown to be an efficient asymmetric catalyst for the glyoxylate-ene reaction with α-methylstyrene to give 98.7% entaniomeric excess and 88% yield even by the use of 0.2 mol% of the complex O.

  甲苯共沸后，由二酚和（Pr i O）2 TiCl 2的溶液经ms 4过滤后，偶然从甲苯中得到了由二酚（binol）衍生的手性钛µ-氧代络合物O，被证明是一种有效的不对称催化剂。乙醛酸酯-烯与α-甲基苯乙烯的反应，即使使用0.2 mol％的配合物O，也可得到98.7％的对映异构体过量和88％的产率。
• 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。