(3S)-3-methyl-1,3-dihydroisobenzofuran-1-ol | 290330-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (3S)-3-methyl-1,3-dihydroisobenzofuran-1-ol
• 英文别名: 1-hydroxy-3-methyl-2-oxaindan；(3S)-3-methyl-1,3-dihydro-2-benzofuran-1-ol
• CAS: 290330-28-8
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: GVZFPWCBUWAGHL-AADKRJSRSA-N

物化性质

• 沸点：
  285.8±28.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S)-3-methyl-1,3-dihydroisobenzofuran-1-ol 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以26.0 mg的产率得到(3S)-3-甲基-2-苯并呋喃-1(3H)-酮
  参考文献：
  名称：

  Asymmetric Hydrosilylation of Styrenes Catalyzed by Palladium−MOP Complexes:  Ligand Modification and Mechanistic Studies

  摘要：

  In the palladium-catalyzed asymmetric hydrosilylation of styrene (3a) with trichlorosilane, several chiral monophosphine ligands, (R)-2-diarylphosphino-1,1'-binaphthyls(2a-g), were examined for their enantioselectivity. The highest enantioselectivity was observed in the reaction with (R)-2-bis [3,5-bis(trifluoromethyl)phenyl] phosphino-l,1'-binaphthyl (2g), which gave (S)-1-phenylethanol (5a) of 98% ee after oxidation of the hydrosilylation product, 1-phenyl-1-(trichlorosilyl)ethane (4a). The palladium complex of 2g also efficiently catalyzed the asymmetric hydrosilylation of substituted styrenes on the phenyl ring or at the beta position to give the corresponding chiral benzylic alcohols of over 96% ee. Deuterium-labeling studies on the hydrosilylation of regiospecifically deuterated styrene revealed that P-hydrogen elimination from l-phenylethyl(silyl)palladium intermediate is very fast compared with reductive elimination giving hydrosilylation product when ligand 2g is used. The reaction of o-allylstyrene (9) with trichlorosilane catalyzed by (R)-2g/Pd gave (1S,2R)-1-methyl-2-(trichlorosilylmethyl)indan (10) (91% ee) and (S)-1-(2-(propenyl)phenyl)-1-trichlorosilylethanes (11a and 11b) (95% ee). On the basis of their opposite configurations at the benzylic position, a rationale for the high enantioselectivity of ligand 2g is proposed.

  DOI：

  10.1021/jo001614p
• 作为产物：
  描述：

  (S)-1-(2-((E)-1-propenyl)phenyl)ethanol 在 臭氧 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3S)-3-methyl-1,3-dihydroisobenzofuran-1-ol
  参考文献：
  名称：

  Asymmetric Hydrosilylation of Styrenes Catalyzed by Palladium−MOP Complexes:  Ligand Modification and Mechanistic Studies

  摘要：

  In the palladium-catalyzed asymmetric hydrosilylation of styrene (3a) with trichlorosilane, several chiral monophosphine ligands, (R)-2-diarylphosphino-1,1'-binaphthyls(2a-g), were examined for their enantioselectivity. The highest enantioselectivity was observed in the reaction with (R)-2-bis [3,5-bis(trifluoromethyl)phenyl] phosphino-l,1'-binaphthyl (2g), which gave (S)-1-phenylethanol (5a) of 98% ee after oxidation of the hydrosilylation product, 1-phenyl-1-(trichlorosilyl)ethane (4a). The palladium complex of 2g also efficiently catalyzed the asymmetric hydrosilylation of substituted styrenes on the phenyl ring or at the beta position to give the corresponding chiral benzylic alcohols of over 96% ee. Deuterium-labeling studies on the hydrosilylation of regiospecifically deuterated styrene revealed that P-hydrogen elimination from l-phenylethyl(silyl)palladium intermediate is very fast compared with reductive elimination giving hydrosilylation product when ligand 2g is used. The reaction of o-allylstyrene (9) with trichlorosilane catalyzed by (R)-2g/Pd gave (1S,2R)-1-methyl-2-(trichlorosilylmethyl)indan (10) (91% ee) and (S)-1-(2-(propenyl)phenyl)-1-trichlorosilylethanes (11a and 11b) (95% ee). On the basis of their opposite configurations at the benzylic position, a rationale for the high enantioselectivity of ligand 2g is proposed.

  DOI：

  10.1021/jo001614p

文献信息

• [EN] FUSED IMIDAZOLE AND PYRAZOLE DERIVATIVES AS MODULATORS OF TNF ACTIVITY<br/>[FR] DÉRIVÉS D'IMIDAZOLE ET DE PYRAZOLE CONDENSÉS COMME MODULATEURS DE L'ACTIVITÉ DU TNF
  申请人：UCB BIOPHARMA SPRL

  公开号：WO2015086512A1

  公开（公告）日：2015-06-18

  A series of substituted benzimidazole, imidazo[1,2-α]pyridine and pyrazolo[1,5- α]pyridine derivatives, and analogues thereof, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

  一系列取代苯并咪唑、咪唑并[1,2-α]吡啶和吡唑并[1,5-α]吡啶衍生物及其类似物，作为人类TNFα活性的有效调节剂，因此在治疗和/或预防各种人类疾病方面具有益处，包括自身免疫和炎症性疾病；神经学和神经退行性疾病；疼痛和伤害感知性疾病；心血管疾病；代谢性疾病；眼科疾病；以及肿瘤学疾病。
• Highly Diastereoselective Reaction of Chiral o-(2-(1,3-Oxazolidinyl))benzaldehydes with Alkylmetallic Reagents: Synthesis of Chiral 3-Substituted Phthalides.
  作者：Hiroshi TAKAHASHI、Takeshi TSUBUKI、Kimio HIGASHIYAMA

  DOI：10.1248/cpb.39.3136

  日期：——

  Highly diastereoselective reaction of chiral o-[2-(1, 3-Oxazolidinyl)]benzaldehydes (4-6) with alkylmetallic reagents provides a new synthetic method for chiral 3-alkylphthalides.

  高度非对映选择性的手性o-[2-(1,3-噁唑啉基)]苯甲醛(4-6)与烷基金属试剂反应，为手性3-烷基酞内酯提供了一种新颖的合成方法。
• Fused imidazole and pyrazole derivatives as modulators of TNF activity
  申请人：UCB BIOPHARMA SPRL

  公开号：US10004737B2

  公开（公告）日：2018-06-26

  A series of substituted benzimidazole, imidazo[1,2-α]pyridine and pyrazolo[1,5-α]pyridine derivatives, and analogs thereof, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

  一系列取代的苯并咪唑、咪唑并[1,2-α]吡啶和吡唑并[1,5-α]吡啶衍生物及其类似物是人类 TNFα 活性的强效调节剂，因此可用于治疗和/或预防各种人类疾病，包括自身免疫和炎症性疾病、神经和神经退行性疾病、疼痛和痛觉失调、心血管疾病、代谢性疾病、眼部疾病和肿瘤疾病。
• FUSED IMIDAZOLE AND PYRAZOLE DERIVATIVES AS MODULATORS OF TNF ACTIVITY
  申请人：UCB Biopharma SPRL

  公开号：EP3080120B1

  公开（公告）日：2019-06-19
• Fused Imidazole and Pyrazole Derivatives as Modulators of TNF Activity
  申请人：UCB BIOPHARMA SPRL

  公开号：US20170128445A1

  公开（公告）日：2017-05-11

  A series of substituted benzimidazole, imidazo[1,2-α]pyridine and pyrazolo[1,5-α]pyridine derivatives, and analogues thereof, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.