6-((tert-butyldimethylsilyl)oxy)hexanenitrile | 83067-13-4

• 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: 6-((tert-butyldimethylsilyl)oxy)hexanenitrile
• 英文别名: 6-(dimethyl-tert-butylsilyloxy)-hexane-nitrile；6-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]hexanenitrile；6-[tert-butyl(dimethyl)silyl]oxyhexanenitrile
• CAS: 83067-13-4
• 化学式: C₁₂H₂₅NOSi
• 分子量: 227.422
• InChiKey: GHIXRGNQWNPPOK-UHFFFAOYSA-N

物化性质

• 沸点：
  283.6±23.0 °C(Predicted)
• 密度：
  0.867±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-((tert-butyldimethylsilyl)oxy)hexanenitrile 在 正丁基锂 、 叔丁基磺酰氯 、 bis[rhodium(α,α,α’α’,-tetramethyl-1,3-benzenedipropionic acid)] 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 dimethyl 2-(7-hydroxyhept-1-yn-1-yl)-2-phenylcyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  Gold-Catalyzed Rearrangement of Alkynyl Donor–Acceptor Cyclopropanes To Construct Highly Functionalized Alkylidenecyclopentenes

  摘要：

  A gold-catalyzed 1,7-addition-cyclization-elimination cascade sequence performed on a range of alkynyl-substituted donor-acceptor-type cyclopropanes provides facile entry to highly functionalized exo-alkylidenecyclopentenes under very mild conditions. Isolation of the relevant allyl ether intermediate helped shed light on the reaction's mechanistic course.

  DOI：

  10.1021/acs.orglett.5b00671
• 作为产物：
  描述：

  5-((tert-butyldimethylsilyl)oxy)pentyl 4-methylbenzenesulfonate 生成 6-((tert-butyldimethylsilyl)oxy)hexanenitrile
  参考文献：
  名称：

  SKUBALLA, W.;VORBRUEGGEN, H.;RADUECHEL, B.;LOGE, O.;VISCHER, P.

  摘要：

  DOI：

文献信息

• Thiocyanate radical mediated dehydration of aldoximes with visible light and air
  作者：Yong-Liang Ban、Jian-Ling Dai、Xiao-Ling Jin、Qing-Bao Zhang、Qiang Liu

  DOI：10.1039/c9cc05354a

  日期：——

  We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol

  我们开发了一种通过在室温下从硫氰酸铵和分子氧中原位生成的硫氰酸根来活化醛肟的新方法。用催化量的有机染料壬酸鸟嘌呤作为光催化剂，醛肟的脱水在可见光照射下平稳进行，提供了简单的操作，优异的官能团耐受性和适用于多种腈的无金属方案。
• Prostacyclins and use as medicinal agents
  申请人：Schering Aktiengesellschaft

  公开号：US04364951A1

  公开（公告）日：1982-12-21

  Prostane derivatives of the formula ##STR1## wherein B is straight-chain or branched alkylene of 1-10 carbon atoms, A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--; W is hydroxymethylene or a ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position, and is optionally modified by replacement of the H atom with an ether or acyl group which is conventional for such replacements in prostaglandins and which is readily cleavable at physiological pH's; D and E together are a direct bond or D is straight-chain or branched alkylene of 1-10 carbon atoms, or, such an alkylene of 4-10 carbon atoms containing a double bond in the 2- or 3- position, all of which can optionally be substituted by fluorine, 1,2-methylene, 1,1-trimethylene, or methoxy; E is oxygen, sulfur, --C.tbd.C-- or a direct bond; R.sub.2 is C.sub.1-10, C.sub.2-10 alkenyl, each of which optionally is substituted phenyl, 1-naphthyl or 2-naphthyl, each of which is substituted as defined below; C.sub.4-10 cycloalkyl optionally substituted by C.sub.1-4 alkyl; phenyl, 1-naphthyl, or 2-naphthyl, each of which can optionally be substituted by 1-3 halogen atoms, a phenyl group, 1-3 alkyl groups each independently of 1-4 carbon atoms, or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, C.sub.1 -C.sub.4 -alkoxy, or hydroxy group, or an aromatic 5- or 6-membered heterocyclic ring having one hetero ring atom which is O, N, or S, the remaining atoms being carbon; and R.sub.1 is hydroxy optionally modified as for W above, have valuable vasodilating, anti-hypertensive, and bronchodilating pharmacological properties.

  公式为 ##STR1## 的prostane衍生物，其中B是1-10个碳原子的直链或支链烷基，A是--CH.sub.2 --CH.sub.2 --，trans--CH.dbd.CH--或--C.tbd.C--；W是羟甲基或 ##STR2## 其中OH基团可以在α或β位置，且可以通过取代H原子以ether或acyl基团进行修改，这在prostaglandins中是常规的，并且在生理pH下容易被裂解；D和E一起是直接键，或者D是1-10个碳原子的直链或支链烷基，或者是含有2-或3-位置双键的4-10个碳原子的烷基，所有这些都可以选择性地被氟、1,2-亚甲基、1,1-三亚甲基或甲氧基取代；E是氧、硫、--C.tbd.C--或直接键；R.sub.2是C.sub.1-10、C.sub.2-10烯基，每个烯基可以选择性地被取代为苯基、1-萘基或2-萘基，每个取代如下所定义；C.sub.4-10环烷基可以选择性地被C.sub.1-4烷基取代；苯基、1-萘基或2-萘基，每个可以选择性地被1-3个卤素原子、苯基、1-3个独立的碳原子为1-4的烷基取代，或者是氯甲基、氟甲基、三氟甲基、羧基、C.sub.1-C.sub.4-烷氧基或羟基，或者是具有一个杂环原子的芳香5-或6-成员环，该杂环原子是O、N或S，其余原子是碳；R.sub.1是羟基，可以选择性地按照上述W进行修改，具有有价值的扩血管、降压和支气管扩张药理学特性。
• SKUBALLA, W.;VORBRUEGGEN, H.;RADUECHEL, B.;CASALS, J.;SCHILLINGER, E.;TOW+
  作者：SKUBALLA, W.、VORBRUEGGEN, H.、RADUECHEL, B.、CASALS, J.、SCHILLINGER, E.、TOW+

  DOI：——

  日期：——
• SKUBALLA, WERNER;RADUCHEL, BERND;VORBRUGGEN, HELMUT, TETRAHEDRON LETT., 29,(1988) N 34, C. 4285-4288
  作者：SKUBALLA, WERNER、RADUCHEL, BERND、VORBRUGGEN, HELMUT

  DOI：——

  日期：——
• Gold-Catalyzed Rearrangement of Alkynyl Donor–Acceptor Cyclopropanes To Construct Highly Functionalized Alkylidenecyclopentenes
  作者：Huiyu Chen、Jing Zhang、David Zhigang Wang

  DOI：10.1021/acs.orglett.5b00671

  日期：2015.5.1

  A gold-catalyzed 1,7-addition-cyclization-elimination cascade sequence performed on a range of alkynyl-substituted donor-acceptor-type cyclopropanes provides facile entry to highly functionalized exo-alkylidenecyclopentenes under very mild conditions. Isolation of the relevant allyl ether intermediate helped shed light on the reaction's mechanistic course.