(9-benzyl-1,2,3,4-tetrahydrocarbazol-1-yl)methanol | 666738-07-4

• 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: (9-benzyl-1,2,3,4-tetrahydrocarbazol-1-yl)methanol
• CAS: 666738-07-4
• 化学式: C₂₀H₂₁NO
• 分子量: 291.393
• InChiKey: FKFUBVZENHJDEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  25.16
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (9-benzyl-1,2,3,4-tetrahydrocarbazol-1-yl)methanol 在 吡啶 、 lithium aluminium tetrahydride 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 79.5h， 生成 9-benzyl-1-methyl-1,2,3,4-tetrahydrocarbazole-1-carboxaldehyde
  参考文献：
  名称：

  The Vilsmeier-Haack Reaction on Methyl Homologues of N-Benzyltetrahydrocarbazole (Synthetic Studies on Indoles 52)

  摘要：

  To examine the steric effect in the Vilsmeier-Haack reaction of N-benzyl- 1,2,3,4,-tetrahydrocarbazole (1), the reactions were carried out on three methyl homologues of 1. It was found that 1-methyl- or 4,4-dimethyl group has a large effect on reactivity due to their steric bulkiness. This result shows the importance of an initial attack at the 4a-position for the formation of these products.

  DOI：

  10.3987/com-03-s22
• 作为产物：
  描述：

  (9-benzyl-1,2,3,4-tetrahydrocarbazol-1-yl)carboxaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 (9-benzyl-1,2,3,4-tetrahydrocarbazol-1-yl)methanol
  参考文献：
  名称：

  The Vilsmeier-Haack Reaction on Methyl Homologues of N-Benzyltetrahydrocarbazole (Synthetic Studies on Indoles 52)

  摘要：

  To examine the steric effect in the Vilsmeier-Haack reaction of N-benzyl- 1,2,3,4,-tetrahydrocarbazole (1), the reactions were carried out on three methyl homologues of 1. It was found that 1-methyl- or 4,4-dimethyl group has a large effect on reactivity due to their steric bulkiness. This result shows the importance of an initial attack at the 4a-position for the formation of these products.

  DOI：

  10.3987/com-03-s22

文献信息

• The Vilsmeier-Haack Reaction on Methyl Homologues of N-Benzyltetrahydrocarbazole (Synthetic Studies on Indoles 52)
  作者：Yasuoki Murakami、Akira Ishii、Hidehiko Ozawa、Hiroko Okahira、Keiko Hosokawa、Tomiko Tashiro、Jin-ichi Muto、Hideharu Suzuki、Masanobu Tani、Yuusaku Yokoyama

  DOI：10.3987/com-03-s22

  日期：——

  To examine the steric effect in the Vilsmeier-Haack reaction of N-benzyl- 1,2,3,4,-tetrahydrocarbazole (1), the reactions were carried out on three methyl homologues of 1. It was found that 1-methyl- or 4,4-dimethyl group has a large effect on reactivity due to their steric bulkiness. This result shows the importance of an initial attack at the 4a-position for the formation of these products.