(-)-nitraraine | 126524-15-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 柯楠因类生物碱
• 英文名称: (-)-nitraraine
• 英文别名: nitraraine；yohimb-16-en-16-yl-methanol；Alloyohimb-16-en-16-methanol；[(1S,15S,20S)-1,3,11,12,14,15,16,17,20,21-decahydroyohimban-19-yl]methanol
• CAS: 126524-15-0
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: ZRYNKHIKQVFQAE-FMEYXAORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (-)-nitraraine 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 以75%的产率得到(+/-)-dihydronitraraine
  参考文献：
  名称：

  Takano, Seiichi; Samizu, Kiyohiro; Sugihara, Takumichi, Chemistry Letters, 1989, p. 1777 - 1780

  摘要：

  DOI：
• 作为产物：
  描述：

  (5S,6S)-5-Formyl-6-(2-oxo-2-pyrrolidin-1-yl-ethyl)-cyclohex-1-enecarboxylic acid methyl ester 在 sodium tetrahydroborate 、 二异丁基氢化铝 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 2.0h， 生成 (-)-nitraraine
  参考文献：
  名称：

  Takano, Seiichi; Samizu, Kiyohiro; Sugihara, Takumichi, Chemistry Letters, 1989, p. 1777 - 1780

  摘要：

  DOI：

文献信息

• Stereocontrolled Annulations of Indolo[2,3-<i>a</i>]quinolizidine-Derived Lactams with a Silylated Nazarov Reagent: Access to Allo and Epiallo Yohimbine-Type Derivatives
  作者：Federica Arioli、Maria Pérez、Celeste Are、Carolina Estarellas、F. Javier Luque、Joan Bosch、Mercedes Amat

  DOI：10.1002/chem.201501912

  日期：2015.9.14

  The facial selectivity of double Michael addition reactions of the silylated Nazarov reagent 4 to unsaturated indolo[2,3‐a]quinolizidine lactams 3 has been studied. Pentacyclic 3‐H/15‐H trans adducts 5 are generated from Nind‐unsubstituted lactams, but the corresponding cis isomers 6 are formed when the indole nitrogen has a tert‐butyloxycarbonyl (Boc) substituent. This reversal in the facial selectivity

  已研究了甲硅烷基化的Nazarov试剂4对不饱和吲哚[2,3- a ]喹诺唑烷内酰胺3的两次迈克尔加成反应的面部选择性。五环3-H / 15-H反式加合物5个从产生Ñ IND -未被取代的内酰胺，但相应的顺式的异构体6时的吲哚氮具有形成叔‐丁氧羰基（Boc）取代基。通过理论计算已经合理地消除了环形表面选择性的这种逆转，这表明在立体电子控制下的初始亲核攻击受到了庞大Boc基团的阻碍。五环Nazarov衍生的加合物的合成有用性通过将其转化为异源和Epiallo育亨宾型靶标而得到证明。
• Alkaloids from Nitraria schoberi. O-acetylnitraraine
  作者：T. S. Tulyaganov、N. M. Kozimova

  DOI：10.1007/s10600-005-0211-y

  日期：2005.9

  The new alkaloid O-acetylnitraraine was isolated from the aerial part of Nitraria schoberi. Its structure was established using spectral data and chemical transformations.

  从 Nitraria schoberi 的气生部分分离出了新的生物碱 O-乙酰基硝基呋喃。利用光谱数据和化学变化确定了它的结构。
• A highly effective one-pot bicycloannulation methodology for the synthesis of berban and yohimban systems based on organotin-mediated three-component coupling (N-acylative pentadienylation of C:N bonds)
  作者：Ryohei Yamaguchi、Takashi Hamasaki、Tohru Sasaki、Tetsuo Ohta、Kiitiro Utimoto、Sinpei Kozima、Hidemasa Takaya

  DOI：10.1021/jo00057a028

  日期：1993.2

  A highly effective bicycloannulation methodology for the synthesis of berban and yohimban alkaloid systems is described. Three-component coupling reactions of 2,4-pentadienyltin reagents with C=N bonds and alpha,beta-unsaturated acyl chlorides furnish bicycloannulated products in a one-pot operation. For example, the reactions of 2,4-pentadienyltributyltin (1) with isoquinoline derivatives activated by acryloyl chloride afford the tetracyclic (+/-)-allo-berban systems stereoselectively. Similarly, the reaction of 1 with 3,4-dihydro-beta-carboline (11) gives the pentacyclic (+/-)-allo-yohimban system. The reaction is not affected by the stereochemistry of the 2,4-pentadienyltin reagent. A new substituted 2,4-pentadienyltin reagent, 3-(hydroxymethyl)-2,4-pentadienyltrimethyltin (19), is prepared via 3-(hydroxymethyl)pentadienyl dianion. The three-component coupling reaction of 19 with 11 and acryloyl chloride affords the (+/-)-allo-16-(hydroxymethyl)yohimban system, from which (+/-)-nitraraine is readily synthesized. In addition, 1,3-asymmetric induction leads to the high diastereoselectivity realized in bicycloannulation (up to 94% de) when (S)-3-[(tert-butyldimethylsiloxy)methyl]-3,4-dihydroisoquinoline (27), which is readily derived from L-phenylalanine, is used in the three-component coupling reaction.
• Cascading Single-step Stereoselective Construction of the α-Alloyohimbine Framework: A New Synthesis of (-)-Nitraraine
  作者：Kunio Ogasawara、Hideki Sakagami

  DOI：10.3987/com-00-s(i)7

  日期：——
• TAKANO, SEIICHI;SUMIZU, KIYOHIRO;SUGIHARA, TAKUMICHI;SATOH, SHIGEKI;OGASA+, CHEM. LETT.,(1989) N0, C. 1777-1780
  作者：TAKANO, SEIICHI、SUMIZU, KIYOHIRO、SUGIHARA, TAKUMICHI、SATOH, SHIGEKI、OGASA+

  DOI：——

  日期：——