(+)-7α-acetoxy-7H-yohimbine | 94992-43-5

• 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: (+)-7α-acetoxy-7H-yohimbine
• 英文别名: methyl (1S,10S,15R,18S,19R,20S)-10-acetyloxy-18-hydroxy-11,12,14,15,16,17,18,19,20,21-decahydro-1H-yohimban-19-carboxylate
• CAS: 94992-43-5
• 化学式: C₂₃H₂₈N₂O₅
• 分子量: 412.486
• InChiKey: RYIMHZIVVARLRD-XZEGZVJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  88.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-7α-acetoxy-7H-yohimbine 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 methyl (1S,10S,15R,18S,19R,20S)-10,18-dihydroxy-11,12,14,15,16,17,18,19,20,21-decahydro-1H-yohimban-19-carboxylate
  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 acetate 、 sodium cyanoborohydride 作用下， 以 三氟乙酸 为溶剂， 反应 3.0h， 生成 (+)-7α-acetoxy-7H-yohimbine
  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

• A Reinvestigation of the Oxidative Rearrangement of Yohimbane-Type Alkaloids. Part A. Formation of pseudoindoxyl ( = 1,2-dihydro-3H-indol-3-one) derivatives
  作者：Reto Stahl、Hans-J�rg Borschberg

  DOI：10.1002/hlca.19940770514

  日期：1994.8.10

  Contrary to earlier reports, the base-induced rearrangement of the 7-hydroxy-7H-indolenines derived from ajmalicine (1), yohimbine (5), corynanthine (6), methyl reserpate (16), and methyl isoreserpate (17) in each case furnished not just one, but two epimeric spiro-pseudoindoxyl derivatives which have opposite configuration at the spiro centre C(2). In all cases, the major component was shown by NOE

  与先前的报道相反，来自阿马利辛（1），育亨宾（5），哥丹宁（6），草皮酸甲酯（16）和异二十烷酸甲酯（17）的7-羟基-7 H-吲哚碱的碱基诱导重排。每个案例不仅提供了一个，而且还提供了两个在螺旋中心C（2）具有相反构型的差向异构螺-伪吲哚酚衍生物。在所有情况下，NOE实验均显示其主要成分为A型异构体（羰基位于环C和D定义的平面下方）。热力学不太稳定的乙型pseudoindoxyl差向异构体4，10，12，和22 首次被分离和鉴定。
• 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
• Stereochemical Assignment of Pseudoindoxyl Alkaloids
  作者：Hiromitsu Takayama、Mika Kurihara、Sanan Subhadhirasakul、Mariko Kitajima、Norio Aimi、Shin-ichiro Sakai

  DOI：10.3987/com-95-s27

  日期：——

  The stereochemistries of the C2 and C3 positions in three pseudoindoxyl alkaioids, i.e., mitragynine pseudoindoxyl, yohimbine pseudoindoxyl, and beta-yohimbine pseudoindoxyl, were elucidated by spectroscopic analyses. The CD spectra of these compounds and that of fluorocarpamine showed the antipodal-like curves in the long wavelength region.