(1R*,5R*,12bR*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-methanol | 106498-98-0

• 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: (1R*,5R*,12bR*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-methanol
• 英文别名: (1R*,5R*,12bR*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-methanol；[(1R,12bR)-1-ethyl-3,4,6,7,12,12b-hexahydro-2H-indolo[2,3-a]quinolizin-1-yl]methanol
• CAS: 106498-98-0
• 化学式: C₁₈H₂₄N₂O
• 分子量: 284.401
• InChiKey: BKRBRZLECKMEBD-ROUUACIJSA-N

物化性质

• 熔点：
  220-221 °C
• 沸点：
  446.8±40.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R*,5R*,12bR*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-methanol 在 磷酸 、 potassium tert-butylate 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 以 二乙二醇二甲醚 、 苯 为溶剂， 反应 3.5h， 生成 长春西汀杂质 A
  参考文献：
  名称：

  A new approach to (±)-apovincamine

  摘要：

  DOI：

  10.1016/s0040-4039(01)90451-4
• 作为产物：
  描述：

  [(1R,12bR)-1-ethyl-3,4,6,7,12,12b-hexahydro-2H-indolo[2,3-a]quinolizin-1-yl]methyl acetate 以97%的产率得到
  参考文献：
  名称：

  SZANTAY, CSABA;SZABO, LAJOS;KALAUS, GYORGY;SZOMBATHELYI, ZSOLT;KARPATI, E+

  摘要：

  DOI：

文献信息

• New approaches to the synthesis of eburnane alkaloids
  作者：Y. Langlois、A. Pouilhès、D. Génin、R.Z. Andriamialisoa、N. Langlois

  DOI：10.1016/s0040-4020(01)88616-6

  日期：1983.1

  Aldehyde 12 which is a key precursor of the Eburnane alkaloid vincamine 1 has been prepared in two ways. The first one involves a photochemical rearrangement of a spiro oxaziridine intermediate and the second is based on an imino Diels-Alder reaction followed by a stereo and regioselective alkylation.

  醛12这是象牙烷的关键前体生物碱长春胺1已经以两种方式被制备。第一个涉及螺环恶唑烷中间体的光化学重排，第二个基于亚氨基Diels-Alder反应，然后进行立体和区域选择性烷基化。
• Oxidation of Alcohols with o-Iodoxybenzoic Acid in DMSO: A New Insight into an Old Hypervalent Iodine Reagent
  作者：Marco Frigerio、Marco Santagostino、Simona Sputore、Giovanni Palmisano

  DOI：10.1021/jo00127a036

  日期：1995.11

  The ultracentennial 10-I-4 iodinane oxide IBX (3; o-iodoxybenzoic acid; 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide) represents a new oxidizing-reagent that successfully joins to the large family of known oxidants. IBX, in contrast to other valuable oxidants, is inexpensive to prepare and easy to handle, can tolerate moisture and water, and generally gives very good yields. Furthermore, IBX is mild and chemoselective (primary alcohols are converted into aldehydes with no overoxidation to acids; 1,2-diols are converted to alpha-ketols or alpha-diketones without oxidative cleavage; amino alcohols are oxidized to amino carbonyls, without protection of the amino group; sensitive heterocycles are not affected; various other functional groups are compatible with IBX oxidation). IBX is versatile (it works in various solvents and it is highly sensitive to temperature variations), and its solutions in DMSO are stable enough to carry out the oxidation reaction easily.
• Danieli, Bruno; Lesma, Giordano; Palmisano, Giovanni, Gazzetta Chimica Italiana, 1981, vol. 111, # 7/8, p. 257 - 268
  作者：Danieli, Bruno、Lesma, Giordano、Palmisano, Giovanni

  DOI：——

  日期：——
• Synthesis of Vinca alkaloids and related compounds. 21. Preparation of (.+-.)-eburnamonine, (.+-.)-3-epieburnamonine, and (.+-.)-C-norquebrachamine from a common intermediate
  作者：Gyoergy Kalaus、Numan Malkieh、Ildiko Katona、Maria Kajtar-Peredy、Tibor Koritsanszky、Alajos Kalman、Lajos Szabo、Csaba Szantay

  DOI：10.1021/jo00220a017

  日期：1985.10
• SZANTAY, CSABA;KALAUS, GYORGY;SZABO, LAJOS;EZER, ELEMER;SZPORNY, LASZLO;M+
  作者：SZANTAY, CSABA、KALAUS, GYORGY、SZABO, LAJOS、EZER, ELEMER、SZPORNY, LASZLO、M+

  DOI：——

  日期：——