Methyl 2-[phenyl(piperidin-1-yl)methyl]prop-2-enoate | 53059-47-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl 2-[phenyl(piperidin-1-yl)methyl]prop-2-enoate
• 英文别名: methyl 2-[phenyl(piperidin-1-yl)methyl]prop-2-enoate
• CAS: 53059-47-5
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: NLMYHMOJUCHPPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-[phenyl(piperidin-1-yl)methyl]prop-2-enoate 、 三甲基氰硅烷 在 tris(2,2'-bipyridyl)ruthenium dichloride 、 氧气 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以85%的产率得到
  参考文献：
  名称：

  Visible-light-induced cyanation of aza-Baylis–Hillman adducts: a Michael type addition

  摘要：

  Visible-light-induced aerobic oxidative cyanation of aza-Baylis-Hillman (aza-BH) adducts providing valuable allylic cyanides in good to excellent yields has been developed. The protocol involves in situ formation of 4 pi conjugated iminium ion intermediates, which undergo cyanation at the gamma-position to afford Michael type adducts. This is the first example of visible-light-induced catalytic functionalization of aza-BH adducts using air (O-2) as an economical and ecosustainable oxidant and TMSCN as a convenient and readily available cyanide source. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.121

文献信息

• Visible-light-induced direct α-C(sp 3 )–H thiocyanation of tertiary amines
  作者：Arvind K. Yadav、Lal Dhar S. Yadav

  DOI：10.1016/j.tetlet.2015.10.048

  日期：2015.12

  eosin Y catalyzed aerobic oxidative α-C(sp3)–H thiocyanation of tertiary amines is reported. The reaction proceeds through visible-light-induced in situ generation of the iminium ion followed by attack of −SCN nucleophile. This is the first example of visible-light-initiated formation of C(sp3)–S bond employing organo-photoredox catalysis. Mild reaction conditions and use of air and visible light as the

  可见光诱导的曙红Y催化叔胺的需氧氧化α-C（sp 3）–H硫氰化。该反应通过可见光诱导的原位生成亚胺离子，随后的攻击- SCN亲核体。这是利用有机光氧化还原催化可见光引发的C（sp 3）-S键形成的第一个例子。该方案的主要特点是温和的反应条件以及在室温下使用空气和可见光作为最绿色和可持续的试剂。
• Visible-light-induced cyanation of aza-Baylis–Hillman adducts: a Michael type addition
  作者：Vishnu P. Srivastava、Arvind K. Yadav、Lal Dhar S. Yadav

  DOI：10.1016/j.tetlet.2014.01.121

  日期：2014.3

  Visible-light-induced aerobic oxidative cyanation of aza-Baylis-Hillman (aza-BH) adducts providing valuable allylic cyanides in good to excellent yields has been developed. The protocol involves in situ formation of 4 pi conjugated iminium ion intermediates, which undergo cyanation at the gamma-position to afford Michael type adducts. This is the first example of visible-light-induced catalytic functionalization of aza-BH adducts using air (O-2) as an economical and ecosustainable oxidant and TMSCN as a convenient and readily available cyanide source. (C) 2014 Elsevier Ltd. All rights reserved.