5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-1H-benzindole | 121866-11-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-1H-benzindole
• 英文别名: 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-1H-benzo[f]indole；5,5,8,8-tetramethyl-6,7-dihydro-1H-benzo[f]indole
• CAS: 121866-11-3
• 化学式: C₁₆H₂₁N
• 分子量: 227.349
• InChiKey: GQEAQFXSNFTIPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-1H-benzindole 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 2,3,5,6,7,8-hexahydro-5,5,8,8-tetramethyl-1H-benzindole
  参考文献：
  名称：

  Retinobenzoic acids. 4. Conformation of aromatic amides with retinoidal activity. Importance of trans-amide structure for the activity

  摘要：

  N-Methylation of two retinoidal amide compounds, 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl]benz oic acid (3, Am80) and 4-[[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2- naphthalenyl)carbonyl]amino]benzoic acid (5, Am580), resulted in the disappearance of their potent differentiation-inducing activity on human promyelocytic leukemia cell line HL-60. Studies with 1H NMR and UV spectroscopy indicated that large conformational differences exist between the active secondary amides and the inactive N-methyl amides. From a comparison of the spectroscopic results of these amides with those of stilbene derivatives, the conformations of the active amides are expected to resemble that of (E)-stilbene, whereas the inactive amides resemble the Z isomer: 3 (Am80) and 5 (Am580) have a trans-amide bond and their whole structures are elongated, while the N-methylated compounds [4 (Am90) and 6 (Am590)] have a cis-amide bond, resulting in the folding of the two benzene rings. These structures in the crystals were related to those in solution by 13C NMR spectroscopic comparison between the two phases (solid and solution).

  DOI：

  10.1021/jm00130a011
• 作为产物：
  描述：

  1,1,4,4,6-pentamethyl-7-nitro-1,2,3,4-tetrahydronaphthalene 在 palladium on activated charcoal 氢气 作用下， 反应 24.33h， 生成 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-1H-benzindole
  参考文献：
  名称：

  Retinobenzoic acids. 4. Conformation of aromatic amides with retinoidal activity. Importance of trans-amide structure for the activity

  摘要：

  N-Methylation of two retinoidal amide compounds, 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl]benz oic acid (3, Am80) and 4-[[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2- naphthalenyl)carbonyl]amino]benzoic acid (5, Am580), resulted in the disappearance of their potent differentiation-inducing activity on human promyelocytic leukemia cell line HL-60. Studies with 1H NMR and UV spectroscopy indicated that large conformational differences exist between the active secondary amides and the inactive N-methyl amides. From a comparison of the spectroscopic results of these amides with those of stilbene derivatives, the conformations of the active amides are expected to resemble that of (E)-stilbene, whereas the inactive amides resemble the Z isomer: 3 (Am80) and 5 (Am580) have a trans-amide bond and their whole structures are elongated, while the N-methylated compounds [4 (Am90) and 6 (Am590)] have a cis-amide bond, resulting in the folding of the two benzene rings. These structures in the crystals were related to those in solution by 13C NMR spectroscopic comparison between the two phases (solid and solution).

  DOI：

  10.1021/jm00130a011

文献信息

• 화합물 및 이를 포함하는 유기 발광 소자
  申请人：LG CHEM, LTD. 주식회사 엘지화학(120010134563) Corp. No ▼ 110111-2207995BRN ▼107-81-98139

  公开号：KR20210043468A

  公开（公告）日：2021-04-21

  본 명세서는 화학식 1의 화합물 및 이를 포함한 유기 발광 소자를 제공한다.

  本规范提供了化学式1的化合物及包含该化合物的有机发光器件。