methyl 2-allyl-3-hydroxy-3-phenylpropionate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 2-allyl-3-hydroxy-3-phenylpropionate
• 英文别名: rel-(2R,3R)-methyl 2-allyl-3-hydroxy-3-phenylpropanoate；methyl (SR)-2(SR)-[hydroxy(phenyl)methyl]pent-4-enoate；methyl (2S)-2-[(S)-hydroxy(phenyl)methyl]pent-4-enoate
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: NWZFYYYCVRWXTK-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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-allyl-3-hydroxy-3-phenylpropionate 在 锂硼氢 、 Schwartz's reagent 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.75h， 生成 tert-butyldiphenyl{[(1RS,2RS)-2-phenylcyclopentyl]methoxy}silane
  参考文献：
  名称：

  Convergent Evolution of Diastereomeric Mixtures of 5-Methoxy-pentylzirconocenes toward Trans-1,2-substituted Cyclopentanes

  摘要：

  DOI：

  10.1021/acs.orglett.0c03998
• 作为产物：
  描述：

  (E)-(S)-2-((S)-Hydroxy-phenyl-methyl)-5-tributylstannanyl-pent-3-enoic acid methyl ester 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2-allyl-3-hydroxy-3-phenylpropionate
  参考文献：
  名称：

  Original Synthesis of 1,2-Oxathiolan-2-oxides and Vinyl Cyclopropane Carboxylic Esters

  摘要：

  1,2-氧硫杂环戊烷-2-氧化物或乙烯基环丙烷羧酸酯是以 2,4-戊二烯酸甲酯、三丁基斯坦尼锂和羰基化合物为原料，通过化学选择性制备而成，而且产量相当高。在制备过程中，后者会正式脱氧，并扮演碳烯化合物的角色。

  DOI：

  10.1055/s-1997-6140

文献信息

• Stereoselective [3,3]-Sigmatropic Rearrangement Promoted by the Metal [1,3]-Shift of Binuclear Fischer Carbene Complexes
  作者：Ken Kamikawa、Atsushi Tachibana、Yasunori Shimizu、Kazuya Uchida、Masaru Furusho、Motokazu Uemura

  DOI：10.1021/ol048171m

  日期：2004.11.1

  Reaction of chiral homobinuclear Fischer chromium carbene complexes with allyl alcohol in the presence of NaH and the following oxidative demetalation gave alpha-allyl esters in up to 97% ee via [3,3]-sigmatropic rearrangement reaction promoted by the metal 1,3-shift. On the other hand, chiral heterobinuclear tungsten carbene complexes with arene chromium complexes afforded alpha-allyl-beta-hydroxy

  在NaH存在下手性同双核Fischer铬卡宾络合物与烯丙醇的反应以及随后的氧化脱金属反应，通过金属1,3-促进的[3,3]-σ重排反应，生成高达97％ee的α-烯丙基酯。转移。另一方面，通过相同的反应顺序，手性杂双核钨卡宾配合物与芳烃铬配合物可提供高达92/8 dr的主要产物α-烯丙基-β-羟基酯。
• Asymmetric aldol reactions from titanium enolates of α-seleno ketones and esters
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Claudio Santi、Luana Bagnoli、Andrea Temperini

  DOI：10.1016/j.tetasy.2003.12.035

  日期：2004.3

  Asymmetric aldol condensations using titanium enolates of (R)-camphorselenoacetone and of methyl (R)-camphorselenoacetate are reported. The reactions with aromatic, α,β-unsaturated or aliphatic aldehydes proceed with good chemical yields giving a mixture of the syn and anti aldols. These diastereoisomers were easily separated by column chromatography. The two syn diastereoisomers were obtained in enantiomerically

  使用的（钛烯醇化物的不对称醛醇缩合- [R）-camphorselenoacetone和甲基（[R）-camphorselenoacetate报告。与芳族，α，β-不饱和或脂肪族醛的反应以良好的化学收率进行，得到顺式和反式醇醛的混合物。这些非对映异构体易于通过柱色谱法分离。以对映体纯的形式获得了两种顺式非对映异构体。
• Investigation of a model for 1,2-asymmetric induction in reactions of .alpha.-carbalkoxy radicals: a stereochemical comparison of reactions of .alpha.-carbalkoxy radicals and ester enolates
  作者：David J. Hart、Ramanarayanan Krishnamurthy

  DOI：10.1021/jo00042a029

  日期：1992.7

  The stereochemical course of reductions and allylations of alpha-carbalkoxy radicals with chiral centers at the beta-position are reported. Radicals without polar substituents, with alkoxyl or acetoxyl groups, and with hydroxyl groups at the beta-position were examined. Reactions showed selectivities ranging from low (50:50) to high (99:1). The results are discussed in terms of transition-state models that emphasize the importance of (1) allylic conformational analysis (minimization of A1,3 and A1,2 strain), (2) torisonal strain (minimization of eclipsed interactions), and (3) stereoelectronic effects.
• Convergent Evolution of Diastereomeric Mixtures of 5-Methoxy-pentylzirconocenes toward Trans-1,2-substituted Cyclopentanes
  作者：Aurélien Coelho、Carine Machado-Rodrigues、Jean-Bernard Behr、Jean-Luc Vasse

  DOI：10.1021/acs.orglett.0c03998

  日期：2021.2.5
• Original Synthesis of 1,2-Oxathiolan-2-oxides and Vinyl Cyclopropane Carboxylic Esters
  作者：Alain Krief、Laurent Provins

  DOI：10.1055/s-1997-6140

  日期：1997.6

  1,2-Oxathiolan-2-oxides or vinyl cyclopropane carboxylic esters are prepared chemoselectively and in rather good yields from methyl 2,4-pentadienoate, tributylstannyllithium and carbonyl compounds. The later are formally deoxygenated in the process and play the role of carbenes.

  1,2-氧硫杂环戊烷-2-氧化物或乙烯基环丙烷羧酸酯是以 2,4-戊二烯酸甲酯、三丁基斯坦尼锂和羰基化合物为原料，通过化学选择性制备而成，而且产量相当高。在制备过程中，后者会正式脱氧，并扮演碳烯化合物的角色。