1-tert-butyl-9-fluorenol | 166985-52-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-tert-butyl-9-fluorenol
• 英文别名: 1-tert-butyl-9H-fluoren-9-ol
• CAS: 166985-52-0
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: MFLSDMAOCNFEOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-tert-butyl-9-fluorenol 在 吡啶 、 silver tetrafluoroborate 、 三溴化磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.5h， 生成 ethyl N-(1-tert-butyl-9-fluorenyl)carbamate
  参考文献：
  名称：

  Chemistry of 1-Alkylfluorenylidenes. Steric Effects on Arylcarbene Reactivities

  摘要：

  9-Diazofluorenes (RDAF, 1) having a series of alkyl (R) groups from Me to tBu at the 1-position were prepared and decomposed to generate the corresponding fluorenylidenes (RFL, 2) under various conditions in order to examine steric effects on the reactivities of carbenes. Thus, in cyclohexane, singlet fluorenylidenes ((1)RFLs) gave 9-cyclohexylfluorenes while triplet states ((3)RFLs) underwent H abstraction to give 9-fluorenyl (RFLH(.)), which eventually led to fluorene (4, RFLH(2)) and 9,9'bifluorenyl (5), and the ratio of the triplet products to the singlet was increased as more bulky R groups were introduced at the 1-position. These results are interpreted in terms of the steric effects on singlet reactivity, which requires formation of two bonds simultaneously. Generation of tBuFL resulted in the almost exclusive formation of intramolecular reaction products which involved not only insertion of carbene into the delta-C-H bonds of the tert-butyl group but also insertion of the 1,5-biradical, followed by neophyl-type rearrangement. The results are understood as indicating that abstraction of the delta-H by (3)tBuFL gains over the concerted intramolecular C-H insertion in (1)tBuFL. Generation of 1-RFL (R = Et, iPr, tBu) in the gas phase at high temperature gave intramolecular reaction products both in singlet and in triplet states, but the ratio of the singlet to the triplet product increased in going from Et to iPr to tBu presumably due to the increased opportunities of (1)FL to be trapped by delta-C-H bonds. Spectroscopic studies using matrix isolation techniques as well as laser flash photolysis were also carried out to gain information on the intermediates.

  DOI：

  10.1021/ja00121a007
• 作为产物：
  描述：

  1-tert-butyl-9-fluorenone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以52%的产率得到1-tert-butyl-9-fluorenol
  参考文献：
  名称：

  Chemistry of 1-Alkylfluorenylidenes. Steric Effects on Arylcarbene Reactivities

  摘要：

  9-Diazofluorenes (RDAF, 1) having a series of alkyl (R) groups from Me to tBu at the 1-position were prepared and decomposed to generate the corresponding fluorenylidenes (RFL, 2) under various conditions in order to examine steric effects on the reactivities of carbenes. Thus, in cyclohexane, singlet fluorenylidenes ((1)RFLs) gave 9-cyclohexylfluorenes while triplet states ((3)RFLs) underwent H abstraction to give 9-fluorenyl (RFLH(.)), which eventually led to fluorene (4, RFLH(2)) and 9,9'bifluorenyl (5), and the ratio of the triplet products to the singlet was increased as more bulky R groups were introduced at the 1-position. These results are interpreted in terms of the steric effects on singlet reactivity, which requires formation of two bonds simultaneously. Generation of tBuFL resulted in the almost exclusive formation of intramolecular reaction products which involved not only insertion of carbene into the delta-C-H bonds of the tert-butyl group but also insertion of the 1,5-biradical, followed by neophyl-type rearrangement. The results are understood as indicating that abstraction of the delta-H by (3)tBuFL gains over the concerted intramolecular C-H insertion in (1)tBuFL. Generation of 1-RFL (R = Et, iPr, tBu) in the gas phase at high temperature gave intramolecular reaction products both in singlet and in triplet states, but the ratio of the singlet to the triplet product increased in going from Et to iPr to tBu presumably due to the increased opportunities of (1)FL to be trapped by delta-C-H bonds. Spectroscopic studies using matrix isolation techniques as well as laser flash photolysis were also carried out to gain information on the intermediates.

  DOI：

  10.1021/ja00121a007

文献信息

• Fucosidase inhibitors
  申请人：HORIZON ORPHAN LLC

  公开号：US10308607B2

  公开（公告）日：2019-06-04

  The present disclosure relates, in general, to compounds useful as inhibitors of fucosidase enzymes, and to methods and compositions for the treatment of tumors or cancers, such as liver disorders and liver tumors (e.g., hepatocellular carcinoma), with a compound as disclosed herein.

  本公开总体上涉及作为岩藻糖苷酶抑制剂的化合物，以及用本文公开的化合物治疗肿瘤或癌症，如肝脏疾病和肝脏肿瘤（如肝细胞癌）的方法和组合物。
• FUCOSIDASE INHIBITORS
  申请人：RAPTOR PHARMACEUTICALS INC.

  公开号：US20170029376A1

  公开（公告）日：2017-02-02

  The present disclosure relates, in general, to compounds useful as inhibitors of fucosidase enzymes, and to methods and compositions for the treatment of tumors or cancers, such as liver disorders and liver tumors (e.g., hepatocellular carcinoma), with a compound as disclosed herein.
• US9951013B2
  申请人：——

  公开号：US9951013B2

  公开（公告）日：2018-04-24