tert-butyl N-[(4-bromophenyl)[(4-methylbenzene)sulfonyl]methyl]carbamate | 1071051-64-3

• 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 N-[(4-bromophenyl)[(4-methylbenzene)sulfonyl]methyl]carbamate
• CAS: 1071051-64-3
• 化学式: C₁₉H₂₂BrNO₄S
• 分子量: 440.358
• InChiKey: OMHIYTUPGOPCLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(4-bromophenyl)[(4-methylbenzene)sulfonyl]methyl]carbamate 在 palladium diacetate 、 caesium carbonate 、 （4R，4''R，5S，5''S）-2,2''-（1-甲基亚乙基）双[4,5-二氢-4,5-二苯基恶唑] 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 24.0h， 生成 tert-butyl N-[(1R,2S)-1-(4-bromophenyl)-2-(5-nitropyridin-2-yl)-3-phenylpropyl]carbamate
  参考文献：
  名称：

  Diastereo- and Enantioselective Pd(II)-Catalyzed Additions of 2-Alkylazaarenes to N-Boc Imines and Nitroalkenes

  摘要：

  A chiral Pd(II)-bis(oxazoline) complex was found to be highly effective in promoting the first direct diastereo- and enantioselective addition of alkylazaarenes to N-Boc aldimines and nitroalkenes under mild conditions. Deprotection of Boc-protected products proceeded readily to provide amines in high yields.

  DOI：

  10.1021/ja3083494
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 ammonium hydroxide 作用下， 以 甲醇 、 甲酸 、 乙醇 、 水 为溶剂， 反应 90.58h， 生成 tert-butyl N-[(4-bromophenyl)[(4-methylbenzene)sulfonyl]methyl]carbamate
  参考文献：
  名称：

  Diastereo- and Enantioselective Pd(II)-Catalyzed Additions of 2-Alkylazaarenes to N-Boc Imines and Nitroalkenes

  摘要：

  A chiral Pd(II)-bis(oxazoline) complex was found to be highly effective in promoting the first direct diastereo- and enantioselective addition of alkylazaarenes to N-Boc aldimines and nitroalkenes under mild conditions. Deprotection of Boc-protected products proceeded readily to provide amines in high yields.

  DOI：

  10.1021/ja3083494

文献信息

• Enantioselective Reaction between 2-(Cyanomethyl)azaarenes and <i>N</i>-Boc-amino Sulfones
  作者：Kezhou Wang、Chao Chen、Xihong Liu、Dan Li、Tianyu Peng、Xin Liu、Dongxu Yang、Linqing Wang

  DOI：10.1021/acs.orglett.8b02205

  日期：2018.9.7

  benzothiazole or benzoxazole were designed and synthesized for asymmetric α-functionalization with N-Boc-amino sulfones. The Mannich adducts were obtained in high yields with good diastereo- and enantioselectivities. Aryl-substituted amino sulfones were tolerated under the current conditions, and the reaction can be performed on gram scale in good results.

  设计并合成了一系列含有苯并噻唑或苯并恶唑的2-（氰基甲基）氮杂芳烃，用于用N -Boc-氨基砜进行不对称α-官能化。曼尼希加合物以高收率获得，具有良好的非对映选择性和对映选择性。在当前条件下可以耐受芳基取代的氨基砜，并且该反应可以以克为单位进行，结果良好。
• Highly cis-selective synthesis of iodo-aziridines using diiodomethyllithium and in situ generated N-Boc-imines
  作者：James A. Bull、Tom Boultwood、Thomas A. Taylor

  DOI：10.1039/c2cc37029h

  日期：——

  The first preparation of iodoaziridines is described. The addition of diiodomethyllithium to N-Boc-imines affords these novel aziridines in high yields. The reaction proceeds in one-pot via a highly diastereoselective cyclisation of an amino gem-diiodide intermediate.

  首次制备了碘代肼烷。将二碘甲基锂加入N-Boc亚胺，可以以高产率获得这些新型肼烷。反应通过氨基齐头双碘中间体的高度二态选择性环化在一个反应瓶中进行。
• Copper-catalyzed borylative coupling of vinylazaarenes and N-Boc imines
  作者：Joshua J. Smith、Daniel Best、Hon Wai Lam

  DOI：10.1039/c6cc00603e

  日期：——

  Diastereoselective Cu-catalyzed three-component couplings of vinylazaarenes, B₂(pin)₂, and N-Boc imines are described.

  描述了具有立体选择性的Cu催化的三组分偶联反应，包括乙烯基氮杂芳烃、B₂(pin)₂和N-Boc亚胺。
• N-Heterocyclic carbene-catalyzed tandem aza-benzoin/Michael reactions: on site reversal of the reactivity of N-Boc imines
  作者：Ke-Jia Wu、Gong-Qiang Li、Yi Li、Li-Xin Dai、Shu-Li You

  DOI：10.1039/c0cc01769h

  日期：——

  A tandem NHC-catalyzed aza-benzoin/Michael reaction has been developed as a method to efficiently produce dihydroindenones and pyrrolidinone-containing tricycles. The novel reaction pattern involves tert-butyl aryl(tosyl)methylcarbamates reacting as both electrophile and nucleophile on the same carbon.

  我们开发了一种串联 NHC 催化的偶氮苯甲酸/迈克尔反应，作为高效生产二氢茚酮和含吡咯烷酮的三环化合物的方法。这种新颖的反应模式涉及叔丁基芳基（甲苯基）甲基氨基甲酸酯作为亲电体和亲核体在同一碳上发生反应。
• <i>N</i>-Carbamate Protected α-Amidoalkyl-<i>p</i>-tolylsulfones: Convenient Substrates in the aza-Morita−Baylis−Hillman Reaction
  作者：Anna Gajda、Tadeusz Gajda

  DOI：10.1021/jo801616d

  日期：2008.11.7

  An efficient and practical one-pot approach to aza-Morita-Baylis-Hillman adducts has been developed. The reaction occurs between N-Boc or N-Cbz imines, generated in situ from stable and easy to handle N-Boc or N-Cbz protected alpha-amidoalkyl-p-tolysulfones, and electron-deficient alkenes in the presence of DABCO. The presented procedure eliminates the use of the relatively unstable N-carbamate imines prior to the coupling reaction. The reaction is limited to alpha-amidosulfones derived from aromatic and heteroaromatic aldehydes.