3α-hydroxy-3aβ-(2-hydroxymethyl-4,5-methylenedioxyphenyl)-6β-methoxy-N-methyl-2,3,6,7-tetrahydro-7aH-indole | 73060-68-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3α-hydroxy-3aβ-(2-hydroxymethyl-4,5-methylenedioxyphenyl)-6β-methoxy-N-methyl-2,3,6,7-tetrahydro-7aH-indole
• 英文别名: 3-epitazettadiol；tazettine；egonine；(3aS)-3a-(6-hydroxymethyl-benzo[1,3]dioxol-5-yl)-6c-methoxy-1-methyl-(3ar,7ac)-2,3,3a,6,7,7a-hexahydro-indol-3t-ol；Tazettadiol；(3R,3aS,6S,7aS)-3a-[6-(hydroxymethyl)-1,3-benzodioxol-5-yl]-6-methoxy-1-methyl-3,6,7,7a-tetrahydro-2H-indol-3-ol
• CAS: 73060-68-1
• 化学式: C₁₈H₂₃NO₅
• 分子量: 333.384
• InChiKey: XEEPVFFWNATEGX-IEGACIPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3α-hydroxy-3aβ-(2-hydroxymethyl-4,5-methylenedioxyphenyl)-6β-methoxy-N-methyl-2,3,6,7-tetrahydro-7aH-indole 在 盐酸 、 硫酸 、 silver(l) oxide 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 deoxypretazettine neomethine
  参考文献：
  名称：

  Transformation of tazettine to pretazettine.

  摘要：

  抗白血病活性的Pretazettine (1) 是通过将tazettine (2) 转化为3-epitazettadiol (3) 获得的 [其结构通过环化形成deoxypretazettine (4) 进行确认]，随后对3进行二氧化锰氧化。这一转化确认了pretazettine (1) 的立体化学。

  DOI：

  10.1248/cpb.28.2924
• 作为产物：
  描述：

  多花水仙碱 在 chromium(VI) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 生成 3α-hydroxy-3aβ-(2-hydroxymethyl-4,5-methylenedioxyphenyl)-6β-methoxy-N-methyl-2,3,6,7-tetrahydro-7aH-indole
  参考文献：
  名称：

  Uyeo,S. et al., Chemical and pharmaceutical bulletin, 1963, vol. 11, p. 1065 - 1067

  摘要：

  DOI：

文献信息

• Alkaloid−Fullerene Systems through Photocycloaddition Reactions¹
  作者：Li-Wei Guo、Xiang Gao、Dan-Wei Zhang、Shi-Hui Wu、Hou-Ming Wu、Yong-Jiang Li、Stephen R. Wilson、Christine F. Richardson、David I. Schuster

  DOI：10.1021/jo000156h

  日期：2000.6.1

  The photocycloaddition of tertiary amines to [60]fullerene (C-60) is an interesting and useful reaction. We wished to extend the applications of this type of reaction through an investigation of the photoaddition of alkaloids to C-60 for the purpose of synthesizing novel and complex photoadducts that are difficult to obtain by usual methods. Irradiation of tazettine (2) or gramine (3) with Cao in toluene leads to formation of one monoadduct (6 or 7), whereas scandine (1a) or 10-hydroxyscandine (Ib) reacts with C-60 photochemically to give two products, the expected [6,6] monoadduct (5a, 5b) and a new type of monoadduct with a bis-[6, 6] closed structure (4a, 4b). These new structures were characterized by W-vis, FT-IR, H-1 NMR, C-13 NMR, H-1-H-1 COSY, ROESY, HMQC (heteronuclear multiple-quantum coherence), and HMBC (heteronuclear multiple-bond connectivity) spectroscopy. The techniques of time-of-flight secondary ion MS (TOF-SIMS) and field desorption MS (FD-MS) were used for the mass determination. He-3 NMR analysis of the product mixture from photoaddition of la to C-60 containing a He-3 atom (He-3@C-60) led to two peaks at -9.091 and -11.090 ppm relative to gaseous He-3, consistent with formation of a [6,6]-closed monoadduct and a bis-[6,6] closed adduct. Presumably, the bis-[6, 6] closed adducts are formed by an intramolecular [2 + 2] cycloaddition of the vinyl group to the adjacent 6,6-ring junction of C-60 after the initial photocycloaddition.
• Transformation of tazettine to pretazettine.
  作者：SHIGERU KOBAYASHI、MASARU KIHARA、TETSURO SHINGU、KEIJI SHINGU

  DOI：10.1248/cpb.28.2924

  日期：——

  Pretazettine (1), which shows antileukemic activity, was obtained by conversion of tazettine (2) to 3-epitazettadiol (3) [whose structure was confirmed by its cyclization to deoxypretazettine (4)], followed by manganese dioxide oxidation of 3. The transformation of 2 to 1 confirmed the stereochemistry of pretazettine (1).

  抗白血病活性的Pretazettine (1) 是通过将tazettine (2) 转化为3-epitazettadiol (3) 获得的 [其结构通过环化形成deoxypretazettine (4) 进行确认]，随后对3进行二氧化锰氧化。这一转化确认了pretazettine (1) 的立体化学。
• Uyeo,S. et al., Chemical and pharmaceutical bulletin, 1963, vol. 11, p. 1065 - 1067
  作者：Uyeo,S. et al.

  DOI：——

  日期：——