tert-butyl N-[(4-methylphenyl)sulfonyl-pyridin-3-ylmethyl]carbamate | 1011258-50-6

• 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: tert-butyl N-[(4-methylphenyl)sulfonyl-pyridin-3-ylmethyl]carbamate
• CAS: 1011258-50-6
• 化学式: C₁₈H₂₂N₂O₄S
• 分子量: 362.45
• InChiKey: XDJWIGICIBIRPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(4-methylphenyl)sulfonyl-pyridin-3-ylmethyl]carbamate 、 亚甲基二磷酸四乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.67h， 以88%的产率得到diethyl [2-tert-butoxycarbonylamino-1-(diethoxyphosphoryl)-2-(pyridin-3-yl)ethyl]phosphonate
  参考文献：
  名称：

  A new access to substituted tetraethyl N-Boc 2-aminoethylidene-1,1-bisphosphonates and phosphonyl-substituted aza-Morita–Baylis–Hillman-type adducts

  摘要：

  A general one-pot synthesis of substituted 2-aminoethylidene-1,1-bisphosphonates has been developed. The protocol involves base-induced addition of sodium tetraethyl methylenebisphosphonate to N-Boc imines generated in situ from N-Boc-alpha-amidoalkyl-p-tolylsulfones by the action of sodium hydride. The direct and efficient conversion of the title compounds into aza-Morita-Baylis-Hillman-type adducts has been also elaborated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.072
• 作为产物：
  描述：

  3-吡啶甲醛 、 氨基甲酸叔丁酯 、 sodium 4-methylbenzenesulfinate 在 甲酸 作用下， 以 甲醇 、 水 为溶剂， 以43%的产率得到tert-butyl N-[(4-methylphenyl)sulfonyl-pyridin-3-ylmethyl]carbamate
  参考文献：
  名称：

  Highly cis-selective synthesis of iodo-aziridines using diiodomethyllithium and in situ generated N-Boc-imines

  摘要：

  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。

  DOI：

  10.1039/c2cc37029h

文献信息

• <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.
• 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。
• A new access to substituted tetraethyl N-Boc 2-aminoethylidene-1,1-bisphosphonates and phosphonyl-substituted aza-Morita–Baylis–Hillman-type adducts
  作者：Anna Gajda、Tadeusz Gajda

  DOI：10.1016/j.tet.2007.11.072

  日期：2008.2

  A general one-pot synthesis of substituted 2-aminoethylidene-1,1-bisphosphonates has been developed. The protocol involves base-induced addition of sodium tetraethyl methylenebisphosphonate to N-Boc imines generated in situ from N-Boc-alpha-amidoalkyl-p-tolylsulfones by the action of sodium hydride. The direct and efficient conversion of the title compounds into aza-Morita-Baylis-Hillman-type adducts has been also elaborated. (c) 2007 Elsevier Ltd. All rights reserved.