4,5,6,7-tetrahydro-2H-isoindol-1-ylmethanol | 165247-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4,5,6,7-tetrahydro-2H-isoindol-1-ylmethanol
• CAS: 165247-08-5
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: SRBYWCQUOSAOND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,5,6,7-tetrahydro-2H-isoindol-1-ylmethanol 在 吡啶 、 溶剂黄146 作用下， 反应 1.0h， 生成 hexadecahydrotetrabenzo{b,g,l,q}porphyrin
  参考文献：
  名称：

  带有环外环的卟啉。第8部分†。氮15和碳13标记的2,3：7,8：12,13：17,18-四丁氧基卟啉的合成‡ §

  摘要：

  通过异氰基乙酸丁酯从15 N-甘氨酸制备氮15标记的4,5,6,7-四氢-2 H-异二烯基-1-羧酸丁酯，总产率为46％。该双环中间体被转化为氮15和碳13标记的2,3：7,8：12,13：17,18-四丁烷卟啉，这是用于沉积四氢苯并卟啉的有用模型系统。

  DOI：

  10.1002/jhet.5570340141
• 作为产物：
  描述：

  4,5,6,7-四氢异吲哚-1-羧酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4,5,6,7-tetrahydro-2H-isoindol-1-ylmethanol
  参考文献：
  名称：

  Porphyrin synthesis from nitrocompounds

  摘要：

  DOI：

  10.1016/s0040-4020(01)89062-1

文献信息

• [EN] TAMBJAMINES AND B-RING FUNCTIONALIZED PRODIGININES<br/>[FR] TAMBJAMINES ET PRODIGININES FONCTIONNALISÉES À CYCLE B
  申请人：UNIV PORTLAND STATE

  公开号：WO2016176450A1

  公开（公告）日：2016-11-03

  Embodiments of tambjamines and B-ring functionalized prodiginines are disclosed. Methods of synthesizing and using the disclosed compounds are also disclosed. Some embodiments of the disclosed compounds have antimalarial activity. Certain embodiments of the disclosed compounds have been shown to clear parasitemia in mice, and/or are curative in a single dose without toxicity.

  本文披露了tambjamine和B环功能化的prodiginines的实施例。还披露了合成和使用所披露化合物的方法。所披露化合物的一些实施例具有抗疟活性。已经证明所披露化合物的某些实施例能够清除小鼠体内的寄生虫，或者在单剂量下具有治愈作用且无毒性。
• Porphyrins with exocyclic rings. 2. Synthesis of geochemically significant tetrahydrobenzoporphyrins from 4,5,6,7-tetrahydro-2H-isoindoles
  作者：Donald A. May、Timothy D. Lash

  DOI：10.1021/jo00044a013

  日期：1992.8

  Benzo- and tetrahydrobenzoporphyrins are widespread constituents of oil shales and petroleum. Although the origins of these materials are not known, a case is made for divinylchlorophyll a, a widespread pigment in marine algae, being the precursor to many of these geoporphyrins. Total syntheses of four tetrahydrobenzoporphyrins related to etioporphyrin III are described. Tetrahydroisoindoles were prepared by condensation of isocyanoacetates with 1-nitrocyclohexene in the presence of DBU or by reaction of aminomalonates with 2-formylcyclohexanone. Condensation of 3-unsubstituted 4,5,6,7-tetrahydro-2H-isoindoles 23c and 23d with (acetoxymethyl)pyrroles in the presence of Montmorillonite clay gave dipyrrylmethanes 28a and 36a in excellent yield. Hydrogenolysis of the benzyl esters and subsequent acid-catalyzed condensation with pyrrole aldehydes 37a and/or 37b gave a series of a,c-biladiene dihydrobromides. Copper(II) mediated cyclization of the a,c-biladienes 32, 33, 35, and 38, followed by demetallation with 15% sulfuric acid-trifluoroacetic acid, gave four isomeric tetrahydrobenzoporphyrins 10-13 in unusually high yield. This work provides a general route for the synthesis of these important porphyrin molecular fossils.
• Porphyrin synthesis from nitrocompounds
  作者：Noboru Ono、Hisayuki Kawamura、Masahiro Bougauchi、Kazuhiro Maruyama

  DOI：10.1016/s0040-4020(01)89062-1

  日期：1990.1
• Porphyrins with exocyclic rings. Part 8. Synthesis of nitrogen-15 and carbon-13 labeled 2,3:7,8:12,13:17,18-tetrabutanoporphyrin
  作者：Shaohua Chen、Timothy D. Lash

  DOI：10.1002/jhet.5570340141

  日期：1997.1

  Nitrogen-15 labeled butyl 4,5,6,7-tetrahydro-2H-isoindoIe-1-carboxylate was prepared via butyl iso-cyanoacetate from 15N-glycine in an overall 46% yield. This bicyclic intermediate was converted into nitrogen-15 and carbon-13 labeled 2,3:7,8:12,13:17,18-tetrabutanoporphyrin, a useful model system for the sedimentary tetrahydrobenzoporphyrins.

  通过异氰基乙酸丁酯从15 N-甘氨酸制备氮15标记的4,5,6,7-四氢-2 H-异二烯基-1-羧酸丁酯，总产率为46％。该双环中间体被转化为氮15和碳13标记的2,3：7,8：12,13：17,18-四丁烷卟啉，这是用于沉积四氢苯并卟啉的有用模型系统。
• Nonionic Superbase-Promoted Synthesis of Oxazoles and Pyrroles: Facile Synthesis of Porphyrins and .alpha.-C-Acyl Amino Acid Esters
  作者：Jiansheng Tang、John G. Verkade

  DOI：10.1021/jo00104a041

  日期：1994.12

  The reaction of acyl chlorides or acid anhydrides with isocyanoacetates in the presence of the superior strong nonionic base P(MeNCH(2)CH(2))(3)N (1) gave oxazoles in 98-99% yield. Treatment of the oxazoles with HCl-MeOH gave alpha-C-acyl amino acid esters in 81-82% yield. The reaction of beta-acetoxy-alpha-nitroalkanes or nitroalkenes with isocyanoacetates in the presence of 1 gave pyrroles in 100% yield. The conjugate acid of 1 can be treated with KO-t-Bu to regenerate 1. Treatment of the pyrroles with LiAlH4, followed by PTSA-CH2(OMe)(2) and oxidation gave porphyrins in 65-69% yield. LiCl, which functions both as a strong nucleophile in the S(N)2 demethylation of the 5,5'-bis(methoxycarbonyl)-3,3',4,4'-tetramethyldipyrromethane 22a and as a Lewis acid in the electrophilic substitution cyclization of paraformaldehyde at dipyrromethane, facilitates the combination of four reactions into a one-pot synthesis of octaethylporphyrin in 67% yield from 22a.