(3E)-3-ethylidene-6-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-(4-methylphenyl)sulfonylpiperidin-2-one | 1028300-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3E)-3-ethylidene-6-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-(4-methylphenyl)sulfonylpiperidin-2-one
• CAS: 1028300-04-0
• 化学式: C₂₄H₂₆N₂O₄S
• 分子量: 438.547
• InChiKey: VEJRPFSFCCXGQI-IJUHEHPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3E)-3-ethylidene-6-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-(4-methylphenyl)sulfonylpiperidin-2-one 在 甲醇 、 sodium amalgam 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 magnesium sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 吲哚并[2,3-a]喹嗪,3-乙基-1,2,3,4,6,7,12,12b-八氢-,反-
  参考文献：
  名称：

  An easy ABD→ABCD strategy to indolo[2,3-a]quinolizin-4-one. Synthesis of deplancheine and yohimbane

  摘要：

  The efficient synthesis of indolo[2,3-alpha]quinolizin-4-ones 2 is described in two steps via formal [3 + 3] cycloaddition reaction of alpha-sulfonyl tryptaminylacetamide 4 with various alpha, beta-unsaturated esters 5 and the regioselective reduction of the resulting glutarimides 3 with sodium borohydride then sequent further dehydrated cyclization in the presence of boron trifluoride etherate. The useful building block is applied to synthesize deplancheine (1a) and yohimbane (1b). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.005
• 作为产物：
  描述：

  2-carbethoxy-1,3-butadiene 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.75h， 生成 (3E)-3-ethylidene-6-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-(4-methylphenyl)sulfonylpiperidin-2-one
  参考文献：
  名称：

  An easy ABD→ABCD strategy to indolo[2,3-a]quinolizin-4-one. Synthesis of deplancheine and yohimbane

  摘要：

  The efficient synthesis of indolo[2,3-alpha]quinolizin-4-ones 2 is described in two steps via formal [3 + 3] cycloaddition reaction of alpha-sulfonyl tryptaminylacetamide 4 with various alpha, beta-unsaturated esters 5 and the regioselective reduction of the resulting glutarimides 3 with sodium borohydride then sequent further dehydrated cyclization in the presence of boron trifluoride etherate. The useful building block is applied to synthesize deplancheine (1a) and yohimbane (1b). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.005

文献信息

• An easy ABD→ABCD strategy to indolo[2,3-a]quinolizin-4-one. Synthesis of deplancheine and yohimbane
  作者：Meng-Yang Chang、Chung-Yi Chen、Wen-Shang Chung、Min-Ruei Tasi、Nein-Chen Chang

  DOI：10.1016/j.tet.2004.11.005

  日期：2005.1

  The efficient synthesis of indolo[2,3-alpha]quinolizin-4-ones 2 is described in two steps via formal [3 + 3] cycloaddition reaction of alpha-sulfonyl tryptaminylacetamide 4 with various alpha, beta-unsaturated esters 5 and the regioselective reduction of the resulting glutarimides 3 with sodium borohydride then sequent further dehydrated cyclization in the presence of boron trifluoride etherate. The useful building block is applied to synthesize deplancheine (1a) and yohimbane (1b). (C) 2004 Elsevier Ltd. All rights reserved.