methyl 2-(α-hydroxybenzyl)-3-butenoate

• 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-(α-hydroxybenzyl)-3-butenoate
• 英文别名: methyl erythro-2-(1-hydroxy-1-phenylmethyl)-3-butenoate；methyl syn-2-(hydroxy(phenyl)methyl)but-3-enoate；methyl (2S)-2-[(S)-hydroxy(phenyl)methyl]but-3-enoate
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: HNRNEPKUSWJSGX-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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-(α-hydroxybenzyl)-3-butenoate 在 ammonium persulfate 、 二苯基二硒醚 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以94%的产率得到methyl 2-phenyl-2,5-dihydro-3-furancarboxylate
  参考文献：
  名称：

  烯烃的催化氧杂烯基化-二硒烯化反应-3烯烃立体选择性一锅法转化为2,5-二氢呋喃

  摘要：

  已经开发了仅使用催化量的二苯基二硒化物和过量的过硫酸铵将2-甲氧基羰基-3-链烯醇转化为3-甲氧基羰基-2,5-二氢呋喃的立体选择性多步一锅法。在赤烯醇给反式二氢呋喃，而苏式立体给出相应的顺式产品。起始烯醇的构型是由中间体苯硒基四氢呋喃的构型推导的，后者是由烯醇与化学计算量的苯基硒烯基硫酸盐的反应独立获得的。

  DOI：

  10.1002/(sici)1099-0690(199904)1999:4<797::aid-ejoc797>3.0.co;2-o
• 作为产物：
  描述：

  3-丁烯酸甲酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.33h， 生成 methyl threo-2-(1-hydroxy-1-phenylmethyl)-3-butenoate 、 methyl 2-(α-hydroxybenzyl)-3-butenoate
  参考文献：
  名称：

  Total Regio- and Diastereocontrol in the Aldol Reactions of Dienolborinates

  摘要：

  It is reported that appropriate dienolborinates can provide access to both diastereomers of 2-(hydroxymethyl)but-3-enoates through exclusive alpha-regiocontrol in a non-vinylogous pathway. Contrary to previous reports in which dialkylchloroboranes failed to enolize propanoates, acidity-enhanced but-3-enoates readily undergo enolization, offering unprecedented control over the formation of these valuable synthons. The first example of an aldol reaction in the presence of a phosphine-borane adduct is also reported.

  DOI：

  10.1021/ol400381q

文献信息

• Synthesis of α-alkenyl-β-hydroxy adducts by α-addition of unprotected 4-bromocrotonic acid and amides with aldehydes and ketones by chromium(II)-mediated reactions
  作者：Ludger A. Wessjohann、Harry Wild、Leonildo A. Ferreira、Henri S. Schrekker

  DOI：10.1002/aoc.3488

  日期：2016.8

  The regioselective and diastereoselective chromium(II)‐mediated reactions of 4‐bromocrotonic acid or amides with aldehydes and ketones can proceed without the need to protect protic sites to generate the respective α‐alkenyl‐β‐hydroxy adducts, i.e. formally the addition of the α‐anion of a carboxylic acid or amide to an oxo‐compound is featured. Copyright © 2016 John Wiley & Sons, Ltd.

  可以进行4-溴巴豆酸或酰胺与醛和酮的区域选择性和非对映选择性铬（II）介导的反应，而无需保护质子位点以生成相应的α-烯基-β-羟基加合物，即正式添加具有羧酸或酰胺的α-阴离子与羰基化合物的特征。版权所有©2016 John Wiley＆Sons，Ltd.
• A NEW METHOD FOR THE SYNTHESIS OF β-HYDROXYESTERS BY USING METALLIC TIN
  作者：Taira Harada、Teruaki Mukaiyama

  DOI：10.1246/cl.1982.161

  日期：1982.2.5

  Metallic tin or activated metallic tin, prepared by reduction of stannous chloride with lithium aluminum hydride, smoothly reacts with α-haloesters to yield tin enolates, which in turn react with carbonyl compounds under mild conditions to give, after hydrolysis, β-hydroxyesters in high yields.

  用氢化铝锂还原氯化亚锡制备的金属锡或活化金属锡，与α-卤代酯平稳反应生成烯醇锡，然后在温和条件下与羰基化合物反应，水解后生成β-羟基酯。产量。
• Enantio- and Diastereoselective Synthesis of <i>syn</i>-β-Hydroxy-α-vinyl Carboxylic Esters via Reductive Aldol Reactions of Ethyl Allenecarboxylate with 10-TMS-9-Borabicyclo[3.3.2]decane and DFT Analysis of the Hydroboration Pathway
  作者：Jeremy Kister、Daniel H. Ess、William R. Roush

  DOI：10.1021/ol4025277

  日期：2013.11

  An enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylate esters 3 via the reductive aldol reaction of ethyl allenecarboxylate (2) with 10-trimethylsilyl-9-borabicyclo[3.3.2]decane (1R) has been developed. Density functional theory calculations suggest that the allene hydroboration involves the 1,4-reduction of 2 with the 1R, leading directly to dienolborinate Z-(O)-8a.

  通过丙二烯羧酸乙酯 ( 2 ) 与 10-三甲基甲硅烷基-9-硼双环 [3.3.2] 癸烷 ( 1R )的还原醛醇反应，对映选择性和非对映选择性合成顺-β-羟基-α-乙烯基羧酸酯3 . 密度泛函理论计算表明丙二烯硼氢化反应涉及2与1R的 1,4-还原，直接导致二烯硼酸Z -(O)- 8a。
• Cha, Joo Hwan; Pae, Ae Nim; Choi, Kyung Il Il, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 17, p. 2079 - 2081
  作者：Cha, Joo Hwan、Pae, Ae Nim、Choi, Kyung Il Il、Cho, Yong Seo、Koh, Hun Yeong、Lee, Eun

  DOI：——

  日期：——
• Parra, Margarita; Mestres, Ramon; Aparicio, Domitila, Journal of the Chemical Society. Perkin transactions I, 1989, p. 327 - 332
  作者：Parra, Margarita、Mestres, Ramon、Aparicio, Domitila、Durana, Nieves、Rubiales, Gloria

  DOI：——

  日期：——