t-hexyl chloroformate | 90196-28-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: t-hexyl chloroformate
• 英文别名: 2-Methylpentan-2-yl carbonochloridate；2-methylpentan-2-yl carbonochloridate
• CAS: 90196-28-4
• 化学式: C₇H₁₃ClO₂
• 分子量: 164.632
• InChiKey: SOANSRQQNXHNRD-UHFFFAOYSA-N

物化性质

• 沸点：
  174.8±9.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-去-t-叔丁氧羰基-10-去乙酰基-7,10-O-二{[(2,2,2-三氯乙基)氧基]羰基}多西他赛 、 t-hexyl chloroformate 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Design, synthesis and cytotoxicity of novel 3′-N-alkoxycarbonyl docetaxel analogs

  摘要：

  By-product 9a exhibited potent cytotoxicity against both SK-OV-3 and A549 cell lines. The structure of 9a was characterized using 1D and 2D NMR experiments and confirmed by synthesis to afford a diastereomeric mixture (16a) that was identical to 9a, as well as a pair of diastereomers (R)-16b and (S)-16c. The preliminary SAR study demonstrated that analogs with an (R)-configuration were slightly more potent than analogs with an (S)-configuration. In addition, alpha, alpha-gem-dimethyl analogs 16g-i were the most potent analogs in this series, exhibiting similar potency to docetaxel and greater potency than Taxol against the SK-OV-3 cell line. For the A549 cell line, analogs 16g-i were more potent (>65-fold) than both docetaxel and Taxol. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.007
• 作为产物：
  描述：

  2-甲基-2-戊醇 、 三光气 在 吡啶 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 t-hexyl chloroformate
  参考文献：
  名称：

  Design, synthesis and cytotoxicity of novel 3′-N-alkoxycarbonyl docetaxel analogs

  摘要：

  By-product 9a exhibited potent cytotoxicity against both SK-OV-3 and A549 cell lines. The structure of 9a was characterized using 1D and 2D NMR experiments and confirmed by synthesis to afford a diastereomeric mixture (16a) that was identical to 9a, as well as a pair of diastereomers (R)-16b and (S)-16c. The preliminary SAR study demonstrated that analogs with an (R)-configuration were slightly more potent than analogs with an (S)-configuration. In addition, alpha, alpha-gem-dimethyl analogs 16g-i were the most potent analogs in this series, exhibiting similar potency to docetaxel and greater potency than Taxol against the SK-OV-3 cell line. For the A549 cell line, analogs 16g-i were more potent (>65-fold) than both docetaxel and Taxol. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.007

文献信息

• A Facile Synthesis of Azidoformate<i>via</i>Chloroformate
  作者：Pei-Lin Wu、Chia-Hao Su、Yi-Jeng Gu

  DOI：10.1002/jccs.200000033

  日期：2000.2

  This work synthesized chloroformates by slowly adding alcohols into a suspension of trichloromethyl chloroformate, instead of phosgene, along with activated charcoal in tetrahydrofuran. This chloroformylation yielded chloroformates in near quantitative yield. The subsequent reaction between chloroformates and sodium azide in dry acetone produced azidoformates in a high yield.

  这项工作通过将醇缓慢加入氯甲酸三氯甲酯的悬浮液中来合成氯甲酸酯，而不是光气，以及四氢呋喃中的活性炭。这种氯甲酰化以接近定量的产率产生氯甲酸酯。氯甲酸酯和叠氮化钠在无水丙酮中的后续反应以高产率产生叠氮甲酸酯。
• beta-DIHYDROFURAN DERIVING COMPOUND, METHOD FOR PRODUCING beta-DIHYDROFURAN DERIVING COMPOUND OR beta-TETRAHYDROFURAN DERIVING COMPOUND, beta-GLYCOSIDE COMPOUND, METHOD FOR PRODUCING beta GLYCOSIDE COMPOUND, AND METHOD FOR PRODUCING 4'-ETHYNYL D4T AND ANALOGUE COMPOUNDS THEREOF
  申请人：Iriyama Yusuke

  公开号：US20120322995A1

  公开（公告）日：2012-12-20

  The invention provides a process for producing a β-dihydrofuran derivative represented by formula (1) or a β-tetrahydrofuran derivative represented by formula (4), characterized in that the process includes causing a dialkyl dicarbonate, a diaralkyl dicarbonate, or a halide to act on a diol compound represented by formula (2) or (3). The invention also provides a process for producing 4′-ethynyl-2′,3′-didehydro-3′-deoxythymidine or an analog thereof, the process including glycosylation and deprotection.

  该发明提供了一种生产由式（1）表示的β-二氢呋喃衍生物或由式（4）表示的β-四氢呋喃衍生物的过程，其特征在于该过程包括使二烷基二碳酸酯、二芳基二碳酸酯或卤化物作用于由式（2）或（3）表示的二醇化合物。该发明还提供了一种生产4'-乙炔基-2',3'-二去氢-3'-脱氧胸苷或其类似物的过程，包括糖基化和去保护。
• B-DIHYDROFURAN DERIVING COMPOUND, METHOD FOR PRODUCING B-DIHYDROFURAN DERIVING COMPOUND OR B-TETRAHYDROFURAN DERIVING COMPOUND, B -GLYCOSIDE COMPOUND, METHOD FOR PRODUCING B-GLYCOSIDE COMPOUND, AND METHOD FOR PRODUCING 4'-ETHYNYL D4T AND ANALOGUE COMPOUNDS THEREOF
  申请人：Nissan Chemical Industries, Ltd.

  公开号：EP2537839A1

  公开（公告）日：2012-12-26

  The invention provides a process for producing a β-dihydrofuran derivative represented by formula (1) or a β-tetrahydrofuran derivative represented by formula (4), characterized in that the process includes causing a dialkyl dicarbonate, a diaralkyl dicarbonate, or a halide to act on a diol compound represented by formula (2) or (3). The invention also provides a process for producing 4'-ethynyl-2',3'-didehydro-3'-deoxythymidine or an analog thereof, the process including glycosylation and deprotection.

  本发明提供了一种生产由式(1)表示的β-二氢呋喃衍生物或由式(4)表示的β-四氢呋喃衍生物的工艺，其特征在于该工艺包括使二烷基二碳酸酯、二烷基二碳酸酯或卤化物作用于由式(2)或(3)表示的二元醇化合物。本发明还提供了一种生产 4'-乙炔基-2',3'-二脱氢-3'-脱氧胸苷或其类似物的工艺，该工艺包括糖基化和脱保护。
• US9212174B2
  申请人：——

  公开号：US9212174B2

  公开（公告）日：2015-12-15
• Design, synthesis and cytotoxicity of novel 3′-N-alkoxycarbonyl docetaxel analogs
  作者：Jun Chang、Xiao-Dong Hao、Yun-Peng Hao、Hong-Fu Lu、Jian-Ming Yu、Xun Sun

  DOI：10.1016/j.bmcl.2013.10.007

  日期：2013.12

  By-product 9a exhibited potent cytotoxicity against both SK-OV-3 and A549 cell lines. The structure of 9a was characterized using 1D and 2D NMR experiments and confirmed by synthesis to afford a diastereomeric mixture (16a) that was identical to 9a, as well as a pair of diastereomers (R)-16b and (S)-16c. The preliminary SAR study demonstrated that analogs with an (R)-configuration were slightly more potent than analogs with an (S)-configuration. In addition, alpha, alpha-gem-dimethyl analogs 16g-i were the most potent analogs in this series, exhibiting similar potency to docetaxel and greater potency than Taxol against the SK-OV-3 cell line. For the A549 cell line, analogs 16g-i were more potent (>65-fold) than both docetaxel and Taxol. (C) 2013 Elsevier Ltd. All rights reserved.