(E)-tert-butyl(4-chloro-2-methylbut-2-enyloxy)dimethylsilane | 270258-26-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-tert-butyl(4-chloro-2-methylbut-2-enyloxy)dimethylsilane
• 英文别名: (E)-tert-butyl(4-chloro-2-methylbut-2-en-1-yloxy)dimethylsilane；tert-butyl-[(E)-4-chloro-2-methylbut-2-enoxy]-dimethylsilane
• CAS: 270258-26-9
• 化学式: C₁₁H₂₃ClOSi
• 分子量: 234.842
• InChiKey: WBIPPUAGQKKSHM-JXMROGBWSA-N

物化性质

• 沸点：
  256.0±20.0 °C(Predicted)
• 密度：
  0.913±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (E)-tert-butyl(4-chloro-2-methylbut-2-enyloxy)dimethylsilane 在 四丁基氟化铵 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 21.83h， 生成 (E)-4-(5-bromo-2-(methoxymethoxy)phenyl)-2-methylbut-2-en-1-ol
  参考文献：
  名称：

  Synthesis, characterization, and PK/PD studies of a series of spirocyclic pyranochromene BACE1 inhibitors

  摘要：

  The development of 1,3,4,4a,5,10a-hexahydropyrano[3,4-b]chromene analogs as BACE1 inhibitors is described. Introduction of the spirocyclic pyranochromene scaffold yielded several advantages over previous generation cores, including increased potency, reduced efflux, and reduced CYP2D6 inhibition. Compound 13 ( BACE1 IC50 = 110 nM) demonstrated a reduction in CSF Ab in wild type rats after a single dose. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.012
• 作为产物：
  描述：

  一氧化异戊二烯 在 咪唑 、 4-二甲氨基吡啶 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 (E)-tert-butyl(4-chloro-2-methylbut-2-enyloxy)dimethylsilane
  参考文献：
  名称：

  Synthesis, characterization, and PK/PD studies of a series of spirocyclic pyranochromene BACE1 inhibitors

  摘要：

  The development of 1,3,4,4a,5,10a-hexahydropyrano[3,4-b]chromene analogs as BACE1 inhibitors is described. Introduction of the spirocyclic pyranochromene scaffold yielded several advantages over previous generation cores, including increased potency, reduced efflux, and reduced CYP2D6 inhibition. Compound 13 ( BACE1 IC50 = 110 nM) demonstrated a reduction in CSF Ab in wild type rats after a single dose. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.012

文献信息

• Gold-Catalyzed Asymmetric Thioallylation of Propiolates via Charge-Induced Thio-Claisen Rearrangement
  作者：Hanbyul Kim、Jiwon Jang、Seunghoon Shin

  DOI：10.1021/jacs.0c09783

  日期：2020.12.9

  A gold(I)-catalyzed enantioselective thioallylation of propiolates with allyl sulfides is described. The key mechanistic element is a sulfonium-induced Claisen rearrangement which helps minimize the allyl dissociation and render higher enantioselectivity. This protocol features remarkable scope of the allyl moiety, allowing enantiocontrolled synthesis of all-carbon quaternary centers, and exhibits

  描述了金 (I) 催化的丙炔酸酯与烯丙基硫化物的对映选择性硫代烯丙基化。关键的机制元素是锍诱导的克莱森重排，这有助于最大限度地减少烯丙基离解并提供更高的对映选择性。该协议具有显着的烯丙基部分范围，允许全碳四元中心的对映控制合成，并与许多路易斯碱和 π 键表现出卓越的官能团兼容性。Claisen 重排的这种分子间变体同时形成 CS 和 CC 键，为获得有趣的光学活性有机硫化合物提供了有效的途径，这些化合物可以通过乙烯基硫化物作为功能手柄进一步转化。对于烯丙基硫化物，反应速率为零级，这表明可逆抑制，为催化剂提供静止状态。哈米特图显示了与 σp 值的相关性，表明限制周转的 σ 重排，其中硫上电子密度的降低加速了重排。
• 9-Methylgermacrene-B is confirmed as the sex pheromone of the sandfly Lutzomyia longipalpis from Lapinha, Brazil, and the absolute stereochemistry defined as S
  作者：J. Gordon C. Hamilton、Helen C. Ibbotson、Antony M. Hooper、John A. Pickett

  DOI：10.1039/a907910f

  日期：——

  The structure of the sex pheromone produced by the male sandfly Lutzomyia longipalpis, from the Lapinha Cave (Minas Gerais State) region of Brazil, previously proposed tentatively as the novel homosesquiterpene 9-methylgermacrene-B, is confirmed and the absolute stereochemistry defined as S by comparing physical and biological properties of the synthetic enantiomers with the natural product.

  来自巴西米纳斯吉拉斯州的拉皮尼亚洞地区的雄性白蛉Lutzomyia longipalpis产生的性信息素结构，之前暂定为新型同型倍半萜9-甲基germacrene-B，现通过比较合成对映体与天然产物的物理和生物学特性，得到了确认，并将其绝对立体化学定义为S型。
• Mechanistic Studies of IspH in the Deoxyxylulose Phosphate Pathway:  Heterolytic C−O Bond Cleavage at C₄ Position
  作者：Youli Xiao、Zongbao K. Zhao、Pinghua Liu

  DOI：10.1021/ja710245d

  日期：2008.2.1

  c-o bond cleavage at the c4 position for isph-catatyzed reductive dehydration reaction. our kinetic studies also suggest that the c4 hydroxyl group is involved in substrate binding. because the isph-catalyzed reductive dehydration reaction does not fall into the two known classes of unique iron-site-containing [4fe-4s] proteins, aconitase-type and radical sam-type enzymes, isph may represent a new class

  类异戊二烯是自然界中最大和结构最多样化的代谢物组之一。它们的生物合成需要两种前体，异戊烯二磷酸酯 (ipp) 及其异构体二甲基烯丙基二磷酸酯 (dmapp)。ipp 和 dmapp 的合成有两种不同的途径：磷酸脱氧木酮糖 (dxp) 途径和甲羟戊酸 (mva) 途径。更重要的是，这两种途径在不同的王国之间有着明确的分布。大多数致病细菌和原生动物寄生虫利用 dxp 途径，而动物则通过 mva 途径从乙酰可可合成它们的类异戊二烯前体。植物具有 dxp 和 mva 途径。因此，对 dxp 途径酶的机制研究可能会导致开发基于机制的抑制剂，如除草剂、广谱抗生素和抗疟疾药物。dxp 途径中的 isph 催化 (e)-4-羟基-3-甲基-2-丁烯基二磷酸 (hmbpp) 的还原脱水形成 ipp 和 dmapp，这是 dxp 途径的最后一步。最近文献报道的 epr 研究表明 isph 是一种独特的含铁位点
• COMPOUNDS FOR TREATING NEURODEGENERATIVE DISEASES
  申请人：Cook Adam

  公开号：US20120157448A1

  公开（公告）日：2012-06-21

  The invention provides novel tricyclic compounds of Formula I′ that inhibit β-secretase cleavage of APP and are useful as therapeutic agents for treating neurodegenerative diseases.

  该发明提供了一种新型三环化合物I'的公式，它能够抑制β-分泌酶对APP的剪切，并且可用作治疗神经退行性疾病的治疗剂。
• Synthesis, characterization, and PK/PD studies of a series of spirocyclic pyranochromene BACE1 inhibitors
  作者：Matthew Volgraf、Lina Chan、Malcolm P. Huestis、Hans E. Purkey、Michael Burkard、Mary Geck Do、Julie Harris、Kevin W. Hunt、Xingrong Liu、Joseph P. Lyssikatos、Sumeet Rana、Allen A. Thomas、Guy P.A. Vigers、Michael Siu

  DOI：10.1016/j.bmcl.2014.04.012

  日期：2014.6

  The development of 1,3,4,4a,5,10a-hexahydropyrano[3,4-b]chromene analogs as BACE1 inhibitors is described. Introduction of the spirocyclic pyranochromene scaffold yielded several advantages over previous generation cores, including increased potency, reduced efflux, and reduced CYP2D6 inhibition. Compound 13 ( BACE1 IC50 = 110 nM) demonstrated a reduction in CSF Ab in wild type rats after a single dose. (C) 2014 Elsevier Ltd. All rights reserved.