(S)-α-acetoxyphenylacetaldehyde | 83461-63-6

• 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: (S)-α-acetoxyphenylacetaldehyde
• 英文别名: (S)-2-acetoxy-2-phenylacetaldehyde；(S)-formylphenylmethyl acetate；[(1S)-2-oxo-1-phenylethyl] acetate
• CAS: 83461-63-6
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: PDEQMKBZTSKEAH-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (R,E)-3-methyl-1-phenyl-2-heptenyl acetate 在 二甲基硫 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-α-acetoxyphenylacetaldehyde
  参考文献：
  名称：

  Stereospecific, Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Allylic Pivalates To Deliver Quaternary Stereocenters

  摘要：

  Recognizing the importance of all-carbon, quaternary stereocenters in complex molecule synthesis, a stereospecific, nickel-catalyzed cross-coupling of allylic pivalates with arylboroxines to deliver products equipped with quaternary stereocenters and internal alkenes was developed. The enantioenriched allylic pivalate starting materials are readily prepared, and a variety of functional groups can be incorporated on both the allylic pivalate and the arylboroxine. Additional advantages include the use of a commercially available and air-stable Ni(II) salt and BISBI ligand, mild reaction conditions, and high yields and ee's. The observed stereoinversion of this reaction is consistent with an open transition state in the oxidative addition step.

  DOI：

  10.1021/acs.orglett.7b02063

文献信息

• Enantioselective reaction of α-lithiated thiazolidines as new chiral formyl anion equivalents
  作者：Libo Wang、Shuichi Nakamura、Yuji Ito、Takeshi Toru

  DOI：10.1016/j.tetasy.2004.08.010

  日期：2004.10

  The reaction of lithiated N-Boc-thiazolidine and N-Boc-benzothiazolidine with benzophenone in the presence of (−)-sparteine afforded the products with up to 97% ee and 93% ee, respectively. The reaction with various aromatic and aliphatic aldehydes also afforded the products with high enantioselectivity and moderate diastereoselectivity. Each diastereomer could be converted to optically active diols

  在（-）-天冬氨酸的存在下，锂化的N - Boc-噻唑烷和N -Boc-苯并噻唑烷与二苯甲酮的反应分别提供了具有高达97％ee和93％ee的产物。与各种芳族和脂族醛的反应也提供了具有高对映选择性和中等非对映选择性的产物。每种非对映异构体都可以转化为旋光性二醇。因此，锂化的N -Boc-噻唑烷和N -Boc-苯并噻唑烷用作手性甲酰基阴离子等同物。确认反应通过动态热力学拆分途径进行。
• An efficient 1,3-asymmetric induction accompanied with epimerization at the 2-position. Stereoselective reduction of α-substituted β-keto sulfoxides under basic conditions
  作者：Katsuyuki Ogura、Makoto Fujita、Takashi Inaba、Kazumasa Takahashi、Hirotada Iida

  DOI：10.1016/s0040-4039(00)81448-3

  日期：1983.1

  An efficient 1,3-asymetric induction was realized in the reduction of β-keto sulfoxides having various α-substituents with NaBH, under basic conditions and, by the application of this induction, (R)-α-acetoxyphenylacetaldehyde was synthesized.

  在碱性条件下，用NaBH还原具有各种α-取代基的β-酮亚砜可实现有效的1,3-不对称诱导，并通过该诱导作用合成了（R）-α-乙酰氧基苯基乙醛。
• OGURA, KATSUYUKI;FUJITA, MAKOTO;INABA, TAKASHI;TAKAHASHI, KAZUMASA;IIDA, +, TETRAHEDRON LETT., 1983, 24, N 5, 503-506
  作者：OGURA, KATSUYUKI、FUJITA, MAKOTO、INABA, TAKASHI、TAKAHASHI, KAZUMASA、IIDA, +

  DOI：——

  日期：——