tert-butyl N-pent-1-enylcarbamate | 328073-56-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl N-pent-1-enylcarbamate
• CAS: 328073-56-9
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: DMHCUBIDRNFOBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl N-pent-1-enylcarbamate 在 甲基三氯硅烷 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以52%的产率得到C₁₀H₁₈ClNO₂
  参考文献：
  名称：

  Methyltrichlorosilane-DMSO: A Facile and Highly Efficient Recipe for the Chlorination of Enamides and Enecarbamates

  摘要：

  开发了一种简便且高效的方法，通过联合使用三氯甲硅烷和DMSO，对烯酰胺和烯碳酸酯进行氯化，从而实现一锅法合成相应的β-氯烯酰胺和烯碳酸酯，收率高且立体选择性好。该方法操作简便，适用于环状和非环状底物。

  DOI：

  10.1055/s-0029-1218005

文献信息

• A Facile and Efficient Approach to <i>N</i> ‐Protected‐β‐Sulfinyl‐ enamines <i>via C</i> ‐Sulfinylation of Enamides and Enecarbamates
  作者：Yinhui Li、Ke Cheng、Xiaoxia Lu、Jian Sun

  DOI：10.1002/adsc.201000084

  日期：2010.10.9

  A practical method has been developed for the C-sulfinylation of enamides and enecarbamates using sodium phenylsulfinate/methyltrichlorosilane (PhSO2Na/MeSiCl3) as the sulfinylating reagent and N,N-dimethylacetamide (DMAc) as the Lewis base promoter, which allows for the preparation of a variety of N-protected-β-sulfinylenamines in high yields and good stereoselectivities. The Lewis base is found to

  已开发出一种实用的方法，使用苯磺酸钠/甲基三氯硅烷（PhSO 2 Na / MeSiCl 3）作为亚磺酰化试剂，并使用N，N-二甲基乙酰胺（DMAc）作为路易斯碱促进剂，对酰胺和烯氨基甲酸酯进行C-亚磺酰基化。以高收率和良好的立体选择性制备各种N-保护的β-亚磺酰亚胺胺。发现路易斯碱对于活性亚磺酰基化物质（PhSOC1）的原位生成和亚磺酰基化步骤均是重要的。
• Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts
  作者：Aurélien Alix、Claudia Lalli、Pascal Retailleau、Géraldine Masson

  DOI：10.1021/ja304095z

  日期：2012.6.27

  phosphoric acids and chiral calcium phosphates both catalyze highly enantio- and diastereoselective electrophilic α-bromination of enecarbamates to provide an atom-economical synthesis of enantioenriched vicinal haloamines. Either enantiomer can be formed in good yield with excellent diastereo- and enantioselectivity simply by switching the catalyst from a phosphoric acid to its calcium salt.

  不含金属的手性磷酸和手性磷酸钙均可催化烯氨基甲酸酯的高度对映选择性和非对映选择性亲电 α-溴化，以提供对映体富集的邻位卤胺的原子经济合成。只需将催化剂从磷酸转换为钙盐，就可以以良好的收率和优异的非对映选择性和对映选择性形成对映异构体。
• Regioselective Rh(I)-Catalyzed Sequential Hydrosilylation toward the Assembly of Silicon-Based Peptidomimetic Analogues
  作者：Geanna K. Min、Troels Skrydstrup

  DOI：10.1021/jo300904z

  日期：2012.7.20

  A highly regioselective Rh(I)-catalyzed hydrosilylation of enamides is presented. This mild protocol allows access to a wide variety of different arylsilanes with substitution at the beta-position of the enamide and functionalization on the alkyl chain tethered to the silane. This protocol is extended to include a sequential one-pot hydrosilylation. Using diphenylsilane as the appendage point, hydrosilylation of a protected allyl alcohol followed by hydrosilylation of an enamide generates a complex organosilane in one step. This highly convergent strategy to synthesize these functionalized systems now provides a way for the rapid assembly of a diverse collection of silane-based peptidomimetic analogues.
• Trimethylchlorosilane-promoted aza-Mannich reaction of enecarbamates and aldimines
  作者：Pengcheng Wu、Deqin Lin、Xiaoxia Lu、Li Zhou、Jian Sun

  DOI：10.1016/j.tetlet.2009.09.097

  日期：2009.12

  A trimethylchlorosilane-promoted aza-Mannich reaction is reported utilizing enecarbamates as the nucleophile and aromatic N-Boc aldimines as the electrophile. A variety of nucleophiles and electrophiles are tolerated by the reaction conditions, delivering the adduct products in excellent yields with high E-stereoselectivities. (C) 2009 Elsevier Ltd. All rights reserved.
• Methyltrichlorosilane-DMSO: A Facile and Highly Efficient Recipe for the Chlorination of Enamides and Enecarbamates
  作者：Xiaoxia Lu、Jian Sun、Deqing Lin、Ke Cheng

  DOI：10.1055/s-0029-1218005

  日期：2009.11

  A facile and highly efficient method was developed for the chlorination of enamides and enecarbamates with the combined use of methyltrichlorosilane and DMSO, which allowed one-pot production of the corresponding β-chloro enamides and enecarbamates in high yield and good stereoselectivity. This method is easy to operate and suitable for both cyclic and acyclic substrates.

  开发了一种简便且高效的方法，通过联合使用三氯甲硅烷和DMSO，对烯酰胺和烯碳酸酯进行氯化，从而实现一锅法合成相应的β-氯烯酰胺和烯碳酸酯，收率高且立体选择性好。该方法操作简便，适用于环状和非环状底物。