(3aR,7aS)-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-one | 13149-08-1

• 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: (3aR,7aS)-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-one
• 英文别名: (3aR,7aS)-2,3,3a,4,7,7a-hexahydroisoindol-1-one
• CAS: 13149-08-1
• 化学式: C₈H₁₁NO
• 分子量: 137.181
• InChiKey: MEYFTNCFZJBFAP-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3aR,7aS)-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-one 在 N-甲基吗啉氧化物 、 四氧化锇 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.17h， 以80%的产率得到(3aR,5R,6S,7aS)-5,6-dihydroxyoctahydro-1H-isoindol-1-one
  参考文献：
  名称：

  手性恶唑并异吲哚酮内酰胺立体控制合成对映体顺式稠合八氢异吲哚酮

  摘要：

  (±)-羟基内酯1和 0.5 equiv 的 ( R )-苯基甘氨醇的立体异构体和环链互变异构体混合物的动力学控制环缩合提供三环恶唑并异吲哚酮内酰胺 (3 R ,5a S ,9a R ,9b S ) -2a，一种多功能中间体用于进一步立体控制转化以获得对映体纯顺式稠合八氢异吲哚酮。该方法的扩展成功地应用于 5,6-二羟基衍生物 (3a R ,5 R ,6 S ,7a S )- 17的合成。

  DOI：

  10.1021/acs.joc.1c01757
• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 ammonium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 160.0 ℃ 、2.1 MPa 条件下， 反应 15.0h， 生成 (3aR,7aS)-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-one
  参考文献：
  名称：

  Synthesis and Fungistatic Activity of Bicyclic Lactones and Lactams against Botrytis cinerea, Penicillium citrinum, and Aspergillus glaucus

  摘要：

  Six analogues of natural trans-4-butyl-cis-3-oxabicyclo[4.3.0]nonan-2-one (3) and three derivatives, 11, 12, and 13, of Vince lactam (10) were synthesized and tested as fungistatic agents against Botrytis cinerea AM235, Penicillium citrinum AM354, and six strains of Aspergillus. Moreover, bioresolution carried out by means of whole cell microorganisms and commercially available enzymes afforded opposite enantiomerically enriched (-) and (+) isomers of Vince lactam (10), respectively. The effect of compound structures and stereogenic centers on biological activity has been discussed. The highest fungistatic activity was observed for four lactones: 3, 4, 7, and 8 (IC50 = 104.6-115.2 μg/mL) toward B. cinerea AM235. cis-5,6-Epoxy-2-aza[2.2.1]heptan-3-one (13) indicated significant fungistatic activity (IC50 = 107.1 μg/mL) against Aspergillus glaucus AM211. trans-4-Butyl-cis-3-oxabicyclo[4.3.0]nonan-2-one (3) and trans-4-butyl-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (7) exhibited high fungistatic activity (IC50 = 143.2 and 110.2 μg/mL, respectively) against P. citrinum AM354 as well.

  DOI：

  10.1021/jf502148h

文献信息

• Enantioselective Reduction of meso-Cyclic-1,2-dicarboxylic Anhydrides and 1,2-Dicarboximides: Asymmetric Synthesis of Bicyclic Lactones and Hydroxylactams.
  作者：Kenji MATSUKI、Hirozumi INOUE、Akihiko ISHIDA、Mikio TAKEDA、Masako NAKAGAWA、Tohru HINO

  DOI：10.1248/cpb.42.9

  日期：——

  Chiral bicyclic lactones (3, 8, 9) and bicyclic hydroxylactams (10-13) were synthesized by highly enantioselective reduction of meso-cyclic-1, 2-dicarboxylic anhydrides (1, 4) and meso-cyclic-1, 2-dicarboximides (2) with lithium aluminum hydride (LiAlH4)-alcohol(ROH)-(R)- or (S)-1, 1'-bi-2-naphthol complex [(R)- or (S)-BINAL-H(ROH)]. Treatment of the hydroxylactams (10-13) with triethylsilane (Et3SiH) and trifluoroacetic acid (CF3CO2H) gave chiral bicyclic lactams (14, 15) in quantitative yields. Removal of the N-4-methoxyphenyl group of the lactams (14, 15) with cerium(IV) ammonium nitrate (CAN) proceeded smoothly to give the corresponding N-unsubstituted lactams (16, 17) in high optical purity.

  手性双环内酯（3、8、9）和双环羟基内酰胺（10-13）是通过对meso-环状-1,2-二羧酸酐（1、4）和meso-环状-1,2-二羧酰胺（2）进行具有高对映选择性的还原反应，使用锂铝氢化物（LiAlH4）-醇（ROH）-（R）或（S）-1,1'-双-2-萘醇复合物[(R)或(S)-BINAL-H(ROH)]合成的。对羟基内酰胺（10-13）进行三乙基硅烷（Et3SiH）和三氟乙酸（CF3CO2H）的处理，得到了手性双环内酰胺（14、15），产率为定量。在高光学纯度下，用铈(IV)铵硝酸盐（CAN）顺利去除内酰胺（14、15）中的N-4-甲氧基苯基基团，得到相应的N-不取代内酰胺（16、17）。
• Stereocontrolled Synthesis of Enantiopure <i>cis</i>-Fused Octahydroisoindolones via Chiral Oxazoloisoindolone Lactams
  作者：Alberto Marbán-González、Gaspar Maravilla-Moreno、Josué Vazquez-Chavez、Marcos Hernández-Rodríguez、Rodrigo Said Razo-Hernández、Mario Ordóñez、José Luis Viveros-Ceballos

  DOI：10.1021/acs.joc.1c01757

  日期：2021.12.3

  cyclocondensation of stereoisomeric and ring–chain tautomeric mixture of (±)-hydroxylactone 1 and 0.5 equiv of (R)-phenylglycinol provided tricyclic oxazoloisoindolone lactam (3R,5aS,9aR,9bS)-2a, a versatile intermediate for further stereocontrolled transformations to access enantiopure cis-fused octahydroisoindolones. An extension of this methodology was successfully applied to the synthesis of the 5,6-dihydroxy

  (±)-羟基内酯1和 0.5 equiv 的 ( R )-苯基甘氨醇的立体异构体和环链互变异构体混合物的动力学控制环缩合提供三环恶唑并异吲哚酮内酰胺 (3 R ,5a S ,9a R ,9b S ) -2a，一种多功能中间体用于进一步立体控制转化以获得对映体纯顺式稠合八氢异吲哚酮。该方法的扩展成功地应用于 5,6-二羟基衍生物 (3a R ,5 R ,6 S ,7a S )- 17的合成。
• Synthesis and Fungistatic Activity of Bicyclic Lactones and Lactams against <i>Botrytis cinerea</i>, <i>Penicillium citrinum</i>, and <i>Aspergillus glaucus</i>
  作者：Paulina Walczak、Jakub Pannek、Filip Boratyński、Agata Janik-Polanowicz、Teresa Olejniczak

  DOI：10.1021/jf502148h

  日期：2014.8.27

  Six analogues of natural trans-4-butyl-cis-3-oxabicyclo[4.3.0]nonan-2-one (3) and three derivatives, 11, 12, and 13, of Vince lactam (10) were synthesized and tested as fungistatic agents against Botrytis cinerea AM235, Penicillium citrinum AM354, and six strains of Aspergillus. Moreover, bioresolution carried out by means of whole cell microorganisms and commercially available enzymes afforded opposite enantiomerically enriched (-) and (+) isomers of Vince lactam (10), respectively. The effect of compound structures and stereogenic centers on biological activity has been discussed. The highest fungistatic activity was observed for four lactones: 3, 4, 7, and 8 (IC50 = 104.6-115.2 μg/mL) toward B. cinerea AM235. cis-5,6-Epoxy-2-aza[2.2.1]heptan-3-one (13) indicated significant fungistatic activity (IC50 = 107.1 μg/mL) against Aspergillus glaucus AM211. trans-4-Butyl-cis-3-oxabicyclo[4.3.0]nonan-2-one (3) and trans-4-butyl-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (7) exhibited high fungistatic activity (IC50 = 143.2 and 110.2 μg/mL, respectively) against P. citrinum AM354 as well.