methyl (R)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylpropanoate | 357675-06-0

• 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: methyl (R)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylpropanoate
• 英文别名: methyl (3R)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylpropanoate
• CAS: 357675-06-0
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: BFAAFHYSAVXYQT-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (R)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylpropanoate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以95%的产率得到5-hydroxymethyl-4-phenyldihydrofuran-2-one
  参考文献：
  名称：

  Stereoselective Conjugate Addition of Aryl- and Alkenylboronic Acids to Acyclic γ,δ-Oxygen-Substituted α,β-Enoates

  摘要：

  The substrate-controlled Rh-I-catalyzed conjugate addition of aryl- and alkenylboronic acids to alpha,beta-unsaturated esters which bear gamma- and delta-oxygen substituents takes place in a highly anti diastereoselective fashion either when using gamma-hydroxyl unprotected starting materials or when the gamma-oxygen substituent is protected with a nonbulky group. The delta-oxygen substituent plays a role in the stereoselectivity of the reaction, and better results are obtained when this OH-group is protected.

  DOI：

  10.1021/ol7016033
• 作为产物：
  描述：

  (S)-(+)-3-(2,2-二甲基-1,3-二噁戊环-4-基)-反-2-丙烯酸甲酯 、 苯硼酸 在 di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 以90%的产率得到methyl (R)-3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylpropanoate
  参考文献：
  名称：

  Stereoselective Conjugate Addition of Aryl- and Alkenylboronic Acids to Acyclic γ,δ-Oxygen-Substituted α,β-Enoates

  摘要：

  The substrate-controlled Rh-I-catalyzed conjugate addition of aryl- and alkenylboronic acids to alpha,beta-unsaturated esters which bear gamma- and delta-oxygen substituents takes place in a highly anti diastereoselective fashion either when using gamma-hydroxyl unprotected starting materials or when the gamma-oxygen substituent is protected with a nonbulky group. The delta-oxygen substituent plays a role in the stereoselectivity of the reaction, and better results are obtained when this OH-group is protected.

  DOI：

  10.1021/ol7016033

文献信息

• 1,2-Stereochemical Induction in the Pd^II-Catalyzed Conjugate Addition of Boronic Acids
  作者：Silvia Roscales、Francisco Sánchez、Aurelio G. Csákÿ

  DOI：10.1002/ejoc.201403488

  日期：2015.3

  2-chiral induction of the conjugate addition of boronic acids to enantiopure α,β-unsaturated ketones and esters without competition from the Mirozoki–Heck reaction. Bedford's palladacycle was found to control the stereoselectivity without the need for additional chiral ligands. We report that the PdII-catalyzed conjugate addition reaction between boronic acids and acyclic ketones or esters that bear a hydroxyl

  钯 (II) 催化已用于底物控制的 1,2-手性诱导硼酸与对映体纯 α,β-不饱和酮和酯的共轭加成反应，而不受 Mirozoki-Heck 反应的竞争。发现贝德福德的钯环无需额外的手性配体即可控制立体选择性。我们报告说，硼酸和在其 γ 位带有羟基取代基的无环酮或酯（甘油醛衍生物）之间的 PdII 催化的共轭加成反应可以提供高水平的抗立体选择，与之前报道的使用更昂贵的 RhI 催化剂相比. 另一方面，使用在其 γ 位带有氨基取代基的无环酯（丝氨酸衍生物）观察到高水平的顺式立体选择性。在这种情况下，
• A study of conjugate addition to a γ,δ-dioxolanyl-α,β-unsaturated ester
  作者：Guoxia Han、Victor J. Hruby

  DOI：10.1016/s0040-4039(01)00719-5

  日期：2001.6

  Diastereoselective phenylcuprate addition to (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-trans-2-propenoate has been achieved in the presence of lithium bromide, copper(I) cyanide, trimethylsilyl chloride and dimethylsulfide cocatalysts.

  在溴化锂，氰化铜（I），三甲基甲硅烷基的存在下，实现了对（S）-3-（2,2-二甲基-1,3-二氧杂戊-4-基）-反-2-丙酸酯的非对映选择性苯基铜酸酯。氯化物和二甲硫的助催化剂。
• Stereoselective Conjugate Addition of Aryl- and Alkenylboronic Acids to Acyclic γ,δ-Oxygen-Substituted α,β-Enoates
  作者：Amaya Segura、Aurelio G. Csákÿ

  DOI：10.1021/ol7016033

  日期：2007.8.1

  The substrate-controlled Rh-I-catalyzed conjugate addition of aryl- and alkenylboronic acids to alpha,beta-unsaturated esters which bear gamma- and delta-oxygen substituents takes place in a highly anti diastereoselective fashion either when using gamma-hydroxyl unprotected starting materials or when the gamma-oxygen substituent is protected with a nonbulky group. The delta-oxygen substituent plays a role in the stereoselectivity of the reaction, and better results are obtained when this OH-group is protected.