1-hydroxyyohimbine | 366456-76-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 育亨宾生物碱
• 英文名称: 1-hydroxyyohimbine
• 英文别名: methyl (1S,15R,18S,19R,20S)-3,18-dihydroxy-11,12,14,15,16,17,18,19,20,21-decahydro-1H-yohimban-19-carboxylate
• CAS: 366456-76-0
• 化学式: C₂₁H₂₆N₂O₄
• 分子量: 370.448
• InChiKey: ONPJOXHDARFHAD-SCYLSFHTSA-N

物化性质

• 熔点：
  224-226 °C (decomp)(Solv: methanol (67-56-1))
• 沸点：
  586.8±60.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  74.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-hydroxyyohimbine 在 sodium acetate 作用下， 反应 7.0h， 生成 7α-acetoxy-17-O-acetylyohimbine
  参考文献：
  名称：

  Synthesis of 1-Hydroxyyohimbine and Its Novel Skeletal Rearrangement Reaction into Oxindole Derivatives

  摘要：

  1-Hydroxyyohimbine was prepared for the first time. Its skeletal rearrangement reaction either directly into 2-oxindole or into 3-oxindole derivatives by a series of reaction is reported. 1-Hydroxyyohimbine and some of its derivatives showed potent alpha2 blocking activity.

  DOI：

  10.3987/com-01-9226
• 作为产物：
  描述：

  盐酸育亨宾 在 sodium tungstate 、 双氧水 、 sodium cyanoborohydride 作用下， 以 三氟乙酸 为溶剂， 反应 2.0h， 生成 1-hydroxyyohimbine
  参考文献：
  名称：

  Synthesis of 1-Hydroxyyohimbine and Its Novel Skeletal Rearrangement Reaction into Oxindole Derivatives

  摘要：

  1-Hydroxyyohimbine was prepared for the first time. Its skeletal rearrangement reaction either directly into 2-oxindole or into 3-oxindole derivatives by a series of reaction is reported. 1-Hydroxyyohimbine and some of its derivatives showed potent alpha2 blocking activity.

  DOI：

  10.3987/com-01-9226

文献信息

• Rearrangement Reaction in 1-Hydroxyindole Chemistry: A Synthesis of Novel 7-Substituted Yohimbine, and 4a-Substituted 1,2,3,4-Tetrahydro-β-Carboline DerivaTives1
  作者：Masanori Somei、Fumio Yamada、Koichi Noguchi、Kiyoka Kusuno

  DOI：10.3987/com-19-14157

  日期：——

  X-Ray analyses of 1-hydroxyyohimbine derivatives definitely show the deviation of the N(1)—O bond from the indole molecular plane. This fact supports our working hypothesis “bishomoallylic conjugation”. The deviation is responsible for the rearrangement reaction in 1-hydroxyindole chemistry. Effective synthetic method for novel 7 and 7 -heteroarylyohimbine, and 4a and 4a -heteroaryl-1,2,3,4-tetrahydro-carboline

  1-羟基育亨宾衍生物的 X 射线分析明确显示了 N(1)-O 键与吲哚分子平面的偏差。这一事实支持我们的工作假设“双烯丙基共轭”。这种偏差是 1-羟基吲哚化学中重排反应的原因。报道了新型7和7-杂芳基育亨宾以及4a和4a-杂芳基-1,2,3,4-四氢咔啉衍生物的有效合成方法。引言 吲哚是一种具有 sp2 杂化氮的平面杂芳族分子。2 在我们的 1-羟基吲哚假说 3 中，我们预计一旦将羟基引入到其氮上，尤其是在这种情况下
• Nucleophilic Substitution Reaction in Indole Chemistry: A Synthesis of Novel 7b-Substituted Yohimbine and 4aa-Substituted 1,2,3,4-Tetrahydro-b-carboline Derivatives
  作者：Masanori Somei、Katsumasa Yoshino、Fumio Yamada

  DOI：10.3987/com-08-s(n)57

  日期：——

  X-Ray analyses of 1-hydroxyyohimbine derivatives clearly show the deviation of the N(1)¯O bond from the indole molecular plane. This phenomenon supports our working hypothesis "bishomoallylic conjugation". The deviation is responsible for the unprecedented nucleophilic substitution reaction in 1-hydroxyindole chemistry and effected the synthesis of novel 7β-heteroarylyohimbine and 4aa-heteroaryl-l

  1-羟基育亨宾衍生物的 X 射线分析清楚地显示了 N(1)¯O 键与吲哚分子平面的偏差。这种现象支持我们的工作假设“双烯丙基共轭”。该偏差导致 1-羟基吲哚化学中前所未有的亲核取代反应，并影响了从相应的 1-羟基吲哚衍生物合成新型 7β-杂芳基育亨宾和 4aa-杂芳基-1,2,3,4-四氢-β-咔啉衍生物.
• Mechanistic duality of indolyl 1,3-heteroatom transposition
  作者：Yujin Lee、Yun Seung Nam、Soo Young Kim、Jeong Eun Ki、Hong Geun Lee

  DOI：10.1039/d3sc00716b

  日期：——

  A novel mechanistic duality has been revealed from the indolyl 1,3-heteroatom transposition (IHT) of N-hydroxyindole derivatives. A series of in-depth mechanistic investigations suggests that two separate mechanisms are operating simultaneously. Moreover, the relative contribution of each mechanistic pathway, the energy barrier for each pathway, and the identity of the primary pathway were shown to

  N-羟基吲哚衍生物的吲哚基1,3-杂原子转位（ IHT）揭示了一种新的机制二元性。一系列深入的机制研究表明，两个独立的机制同时运作。此外，每个机械途径的相对贡献、每个途径的能量势垒以及主要途径的特性都被证明是基底系统的电子特性的函数。基于所获得的机理理解，开发了一种在吲哚 3 位上通用且有效地引入杂原子的机制驱动策略。所开发的反应具有广泛的底物范围，可提供各种形式的官能化吲哚产物。此外，该方法适用于氧基和氮基官能团的引入。
• 1-Hydroxyyohimbine and Its Derivatives: New Potent a2-Blockers for the Treatment of Erectile Dysfunction
  作者：Masanori Somei、Koichi Noguchi、Katsumasa Yoshino、Koichiro Mori、Mamiko Asada、Fumio Yamada、Yoshio Tanaka、Koki Shigenobu、Katsuo Koike

  DOI：10.3987/com-06-s(o)26

  日期：——

  1-Hydroxyyohimbine and its various derivatives are prepared for the first time. These novel compounds are found to be potent alpha(2)-blockers comparable to yohimbine itself.
• Takayama, Hiromitsu; Seki, Norio; Kitajima, Mariko, Heterocycles, 1992, vol. 33, # 1, p. 121 - 125
  作者：Takayama, Hiromitsu、Seki, Norio、Kitajima, Mariko、Aimi, Norio、Seki, Hiroko、Sakai, Shin-ichiro

  DOI：——

  日期：——