1-bromo-4-methyl-4-triethylsilyloxy-2-pentyne | 210219-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-4-methyl-4-triethylsilyloxy-2-pentyne
• 英文别名: 1-bromo-4-triethylsilyloxy-4-methyl-2-pentyne；(5-bromo-2-methylpent-3-yn-2-yl)oxy-triethylsilane
• CAS: 210219-83-3
• 化学式: C₁₂H₂₃BrOSi
• 分子量: 291.304
• InChiKey: PRSDHEDGXVCVBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-bromo-4-methyl-4-triethylsilyloxy-2-pentyne 、 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene 以 四氢呋喃 为溶剂， 以66%的产率得到1α,3β-bis(tert-butyldimethylsilyloxy)-17-(4-triethylsilyloxy-4-methyl-2-pentynyloxymethyl)androsta-5,7,16-triene
  参考文献：
  名称：

  Vitamin d derivatives

  摘要：

  本发明的目的是提供一种表现出优异生理活性的维生素D衍生物作为药物，特别是作为治疗包括牛皮癣在内的皮肤疾病的药剂，并且具有降低的高钙血症活性。 本发明提供了由通式（1）表示的维生素D衍生物： 其中在通式（1）中，X为氧或硫； R1为氢或通式（2）； R2为氢或烷基； R3和R4为氢或烷基，或者R3和R4共同形成16-和17-位置之间的双键； R5为氢或-OR13，其中R13为氢或保护基；以及 R6为氢或保护基。

  公开号：

  US20030195176A1
• 作为产物：
  描述：

  聚合甲醛 、 2-methyl-2-<(triethylsilyl)oxy>-3-butyne 在 正丁基锂 、 甲基磺酰氯 、 三乙胺 、 lithium bromide 作用下， 生成 1-bromo-4-methyl-4-triethylsilyloxy-2-pentyne
  参考文献：
  名称：

  Development of Analogues of 1α,25‐Dihydroxyvitamin D ₃ with Biased Side‐Chain Orientation: C20 Methylated Des‐C,D‐homo Analogues

  摘要：

  AbstractThe discovery that 1α,25‐dihydroxyvitamin D3 is effective in the inhibition of cellular proliferation and in the induction of cellular differentiation has led to a search for analogues in which these activities and the classical calcemic activity of the hormone are dissociated. In this context, the synthesis and biological evaluation are reported for six CD‐ring modified structural analogues that were conceived so as to enforce a particular orientation of the 25‐hydroxylated side chain. The analogues are characterized by the absence of the C‐ring and the presence of an unnatural six‐membered D‐ring. The biased side‐chain orientations are realized through the stereocontrolled incorporation of methyl substituents at positions C13/C20 and C16/C20. Comparison of the results of the biological evaluation and conformational analysis of the side chain confirms the existence of a relationship between inhibition of MCF‐7 breast cancer cell proliferation and side chain geometry.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200801183

文献信息

• 16-ENE-VITAMIN D DERIVATIVES
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：US20020193616A1

  公开（公告）日：2002-12-19

  The compound of the formula (24): 1 wherein R 9 R 10 may be the same or different and each represent a hydrogen atom or a protecting group.

  化学式（24）的化合物：其中R9和R10可以相同或不同，且均表示氢原子或保护基。
• 16-ene-vitamin D derivatives
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：US20020032340A1

  公开（公告）日：2002-03-14

  A compound having the formula (4): wherein 1 X is oxygen or sulfur, R 9 and R 10 are each a hydrogen or a protecting group, and R 11 is an aliphatic hydrocarbon, a —COR 12 group where R 12 is alkyl, aryl or alkoxy, or a group of formula 2 wherein R 5 and R 6 are each hydrogen or hydroxyl, m is 1 to 4, and n is 0-2.

  一个化合物的化学式为(4)，其中1X是氧或硫，R9和R10分别是氢或保护基团，R11是脂肪烃、—COR12基团（其中R12是烷基、芳基或烷氧基）或化学式2中的基团（其中R5和R6分别是氢或羟基，m为1到4，n为0-2）。
• Intermediates for preparation of 16-ene-vitamin D derivatives
  申请人：Chugei Seiyaku Kabushiki Kaisha

  公开号：US06433200B1

  公开（公告）日：2002-08-13

  Intermediates for the preparation of a vitamin D derivative have the following formulas: wherein R9 and R10 may be the same or different and each represents a hydrogen atom or a protecting group, and in Formula (5) the conjugated double bond may be protected by a protecting group.

  制备维生素D衍生物的中间体具有以下公式：其中R9和R10可以相同也可以不同，分别代表氢原子或保护基，在公式（5）中，共轭双键可以由保护基保护。
• 16-ENE-vitamin D derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US06326503B1

  公开（公告）日：2001-12-04

  A compound having the formula (4): wherein X is oxygen or sulfur, R9 and R10 are each a hydrogen or a protecting group, and R11 is an aliphatic hydrocarbon, a —COR12 group where R12 is alkyl, aryl or alkoxy, or a group of formula wherein R5 and R6 are each hydrogen or hydroxyl, m is 1 to 4, and n is 0-2.

  化合物的化学式为（4）：其中X为氧或硫，R9和R10分别为氢或保护基，R11为脂肪烃、-COR12基团，其中R12为烷基、芳基或烷氧基，或者为式中的基团，其中R5和R6分别为氢或羟基，m为1至4，n为0-2。
• Vitamin D derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US07074777B2

  公开（公告）日：2006-07-11

  The object of the present invention is to provide a vitamin D derivative exhibiting excellent physiological activity as medicines, in particular as therapeutic agents for skin disease including psoriasis, and having decreased hypercalcemic activity. The present invention provides vitamin D derivatives represented by the general Formula (1): wherein in Formula (1), X is oxygen or sulfur; R1 is hydrogen or Formula (2) R2 is hydrogen or alkyl; R3 and R4 are hydrogen or alkyl or R3 and R4 together form a double bond between the 16- and 17-positions; R5 is hydrogen or —OR13 in which R13 is hydrogen or a protecting group; and R6 is hydrogen or a protecting group.

  本发明的目的是提供一种维生素D衍生物，作为药物表现出优异的生理活性，特别是作为治疗皮肤疾病，包括银屑病的治疗剂，并具有降低的高钙血症活性。本发明提供了由通式（1）表示的维生素D衍生物：其中在式（1）中，X是氧或硫；R1是氢或式（2）；R2是氢或烷基；R3和R4是氢或烷基，或R3和R4共同形成16位和17位之间的双键；R5是氢或—OR13，其中R13是氢或保护基；R6是氢或保护基。