tert-butyl 2-phenylselenopropionate | 124929-03-9

• 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: tert-butyl 2-phenylselenopropionate
• 英文别名: t-butyl 2-selenophenylpropionate；tert-Butyl 2-(phenylselanyl)propanoate；tert-butyl 2-phenylselanylpropanoate
• CAS: 124929-03-9
• 化学式: C₁₃H₁₈O₂Se
• 分子量: 285.245
• InChiKey: WLODPZMURJABFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-phenylselenopropionate 在 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 反应 1.17h， 生成 tert-butyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-phenylselanylpropanoate
  参考文献：
  名称：

  The Exocyclic Effect:  Protecting Group Strategy to Enhance Stereoselectivity in Hydrogen Transfer Reactions of Acyclic Free Radicals

  摘要：

  To enhance the diastereoselectivity of the hydrogen transfer reaction of acyclic substrates bearing 1,2- or 1,3-diols, the feasibility of a strategy employing bifunctional protecting groups has been demonstrated. This strategy is based upon the "exocyclic effect" or the significant improvement of anti-selectivity exhibited by the reductions of substrates in which the two substituents (R-1 and Y) at the stereogenic center alpha to the radical center are linked together. A rationale for the excellent facial discrimination of these exocyclic radicals is offered based on an analysis of transition state models, which considers both steric and electronic factors.

  DOI：

  10.1021/jo971595s
• 作为产物：
  描述：

  2-溴丙酸叔丁酯 、 二苯基二硒醚 在 sodium tetrahydroborate 作用下， 生成 tert-butyl 2-phenylselenopropionate
  参考文献：
  名称：

  The Exocyclic Effect:  Protecting Group Strategy to Enhance Stereoselectivity in Hydrogen Transfer Reactions of Acyclic Free Radicals

  摘要：

  To enhance the diastereoselectivity of the hydrogen transfer reaction of acyclic substrates bearing 1,2- or 1,3-diols, the feasibility of a strategy employing bifunctional protecting groups has been demonstrated. This strategy is based upon the "exocyclic effect" or the significant improvement of anti-selectivity exhibited by the reductions of substrates in which the two substituents (R-1 and Y) at the stereogenic center alpha to the radical center are linked together. A rationale for the excellent facial discrimination of these exocyclic radicals is offered based on an analysis of transition state models, which considers both steric and electronic factors.

  DOI：

  10.1021/jo971595s

文献信息

• Highly Enantioselective Synthesis of Both Enantiomers of γ-Substituted Butenolides by Bakers' Yeast Reduction and Lipase-Catalyzed Hydrolysis. Total Synthesis of (3A<i>S</i>,6a<i>S</i>)-Ethisolide, Whisky Lactone, and (−)-Avenaciolide
  作者：Sadao Tsuboi、Jun-ichi Sakamoto、Hiroshi Yamashita、Takashi Sakai、Masanori Utaka

  DOI：10.1021/jo970045r

  日期：1998.2.1

  Reduction of 3-chloro-4-oxoalkanoates 5 with bakers' yeast gave (4S)-3-chloro-4-hydraxyalkanoates, which were hydrolyzed and dehydrochlorinated to give (gamma S)-alkylbutenolides with >96% ee. Reduction of 5 with NaBH4 gave syn-3-chloro-4-hydroxyalkanoate 6. Asymmetric hydrolysis of syn-4-chloro-3-hydroxyalkanoate (+/-)-10 with lipase afforded (3R,4R)-6 and (3S,4S)-10 with high optical purities. Hydrolysis and dehydrochlorination of (3R,4R)-6 gave (gamma R)-alkylbutenolides with >85% ee. Total syntheses of (3aS,6aS)-ethisolide, whisky lactone, and (-)-avenaciolide from these butenolides are described.
• Tsuboi, Sadao; Sakamoto, Jun-ichi; Sakai, Takashi, Chemistry Letters, 1989, p. 1427 - 1428
  作者：Tsuboi, Sadao、Sakamoto, Jun-ichi、Sakai, Takashi、Utaka, Masanori

  DOI：——

  日期：——
• TSUBOI, SADAO;SAKAMOTO, JUN-ICHI;SAKAI, TAKASHI;UTAKA, MASANORI, CHEM. LETT.,(1989) N, C. 1427-1428
  作者：TSUBOI, SADAO、SAKAMOTO, JUN-ICHI、SAKAI, TAKASHI、UTAKA, MASANORI

  DOI：——

  日期：——
• Stereocontrol in Radical Processes through the Exocyclic Effect:  Dual Role of Triethylboron as Radical Initiator and in Situ Derivatization Agent
  作者：Jean-Pierre Bouvier、Grace Jung、Ziping Liu、Brigitte Guérin、Yvan Guindon

  DOI：10.1021/ol015758h

  日期：2001.5.1

  [GRAPHICS]The diastereoselectivity of radical processes involving 1,3-diols is increased significantly with a simple and efficient strategy using the exocyclic effect, Boronate derivatives are successfully formed in situ by treatment of an equimolar amount of Et3B in the presence of oxygen, This step is followed by the mediation of a carbon-centered radical a to the cyclic boronate to give the anti reduced product with high stereocontrol. The sequence is also extended to beta -amino alcohols.
• The Exocyclic Effect:  Protecting Group Strategy to Enhance Stereoselectivity in Hydrogen Transfer Reactions of Acyclic Free Radicals
  作者：Yvan Guindon、Anne-Marie Faucher、Élyse Bourque、Valérie Caron、Grace Jung、Serge R. Landry

  DOI：10.1021/jo971595s

  日期：1997.12.1

  To enhance the diastereoselectivity of the hydrogen transfer reaction of acyclic substrates bearing 1,2- or 1,3-diols, the feasibility of a strategy employing bifunctional protecting groups has been demonstrated. This strategy is based upon the "exocyclic effect" or the significant improvement of anti-selectivity exhibited by the reductions of substrates in which the two substituents (R-1 and Y) at the stereogenic center alpha to the radical center are linked together. A rationale for the excellent facial discrimination of these exocyclic radicals is offered based on an analysis of transition state models, which considers both steric and electronic factors.