(E)-3,3,5-trimethylcyclohexanone oxime | 110828-85-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-3,3,5-trimethylcyclohexanone oxime
• 英文别名: 3,3,5-Trimethylcyclohexanone oxime；3,3,5-trimethylcyclohexanone oxime sodium salt；Isophoron-oxim；(1Z)-3,3,5-Trimethylcyclohexanone oxime；(NE)-N-(3,3,5-trimethylcyclohexylidene)hydroxylamine
• CAS: 110828-85-8
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: SBIKADHZIPDOHC-CSKARUKUSA-N

物化性质

• 熔点：
  78-79 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  231.4±9.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3,3,5-trimethylcyclohexanone oxime 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 Petroleum ether 为溶剂， 反应 4.0h， 生成 N-(Diphenylphosphinyl)-3,3,5-trimethylcyclohexylamine
  参考文献：
  名称：

  Stereoselective Hydride Reductions of Cyclic N-Diphenylphosphinyl Imines. Highly Diastereoselective Syntheses of Protected Primary Amines

  摘要：

  Reduction of N-diphenylphosphinyl imines of variously substituted cyclohexanones, cyclopentanones, and bicyclic ketones with lithium tri-sec-butylborohydride provides highly diastereoselective procedures for the syntheses of N-diphenylphosphinyl amines which represent protected primary amines that can be unmasked by mild acidic cleavage. Attack of cyclohexyl derivatives occurs almost exclusively via equatorial approach to yield axial amine derivatives while cyclopentyl and bicyclic imines are attacked from the less sterically encumbered faces.

  DOI：

  10.1021/jo00128a009
• 作为产物：
  描述：

  3,3,5-三甲基环己酮 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 、 水 为溶剂， 以90%的产率得到(E)-3,3,5-trimethylcyclohexanone oxime
  参考文献：
  名称：

  Stereoselective Hydride Reductions of Cyclic N-Diphenylphosphinyl Imines. Highly Diastereoselective Syntheses of Protected Primary Amines

  摘要：

  Reduction of N-diphenylphosphinyl imines of variously substituted cyclohexanones, cyclopentanones, and bicyclic ketones with lithium tri-sec-butylborohydride provides highly diastereoselective procedures for the syntheses of N-diphenylphosphinyl amines which represent protected primary amines that can be unmasked by mild acidic cleavage. Attack of cyclohexyl derivatives occurs almost exclusively via equatorial approach to yield axial amine derivatives while cyclopentyl and bicyclic imines are attacked from the less sterically encumbered faces.

  DOI：

  10.1021/jo00128a009

文献信息

• Propionic acid esters and herbicidal use thereof
  申请人：Hoffmann-La Roche Inc.

  公开号：US04329488A1

  公开（公告）日：1982-05-11

  Propionic acid esters of the general formula ##STR1## wherein R.sub.1 is hydrogen, alkyl of from 1 to 6 carbon atoms or phenyl, R.sub.2 is alkyl of from 1 to 6 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 6 carbon atoms or phenyl, or R.sub.1 and R.sub.2 together with the carbon atom to which they are attached form a cycloalkane ring containing 4 to 10 carbon atoms which can be mono-, di- or trisubstituted with alkyl of from 1 to 3 carbon atoms, R.sub.3 represents a halogen, trifluoromethyl or nitro, and R.sub.4 and R.sub.5 each represent a hydrogen or halogen atom, processes for their manufacture, herbicidal compositions containing these compounds as the active ingredient and methods of use of the herbicidal compositions are disclosed.

  通用公式##STR1##中的丙酸酯，其中R.sub.1是氢，1至6个碳原子的烷基或苯基，R.sub.2是1至6个碳原子的烷基，2至6个碳原子的烯基，2至6个碳原子的炔基或苯基，或者R.sub.1和R.sub.2与它们连接的碳原子一起形成一个含有4至10个碳原子的环烷烃环，该环可以是单取代、双取代或三取代的，取代基为1至3个碳原子的烷基，R.sub.3代表卤素、三氟甲基或硝基，R.sub.4和R.sub.5各自代表氢或卤素原子，公开了其制备方法、含有这些化合物作为活性成分的除草剂组合物以及除草剂组合物的使用方法。
• Mannich Condensation of 3,3,5-Trimethylcyclohexanone and Its Oxime
  作者：S. S. Koval'skaya、N. G. Kozlov、A. V. Tkachev

  DOI：10.1007/s11178-006-0045-5

  日期：2005.12

  Mannich condensation of 3,3,5-trimethylcyclohexanone with paraformaldehyde and dimethylamine or benzylamine hydrochloride involves both activated methylene group in the initial ketone to give compounds with equatorial aminomethyl substituent. The major isomer is that formed by addition at the less sterically hindered carbon atom. Likewise, Mannich condensation of the E and Z isomers of 3,3,5-trimethylcyclohexanone oxime react at both methylene groups, and the addition of aminomethyl fragment occurs preferentially at that methylene group which is located more closely to the oxime hydroxy group.

  3,3,5-三甲基环己酮与多聚甲醛和二甲胺或盐酸苄胺的曼尼希缩合涉及初始酮中的两个活化亚甲基，得到具有平位氨甲基取代基的化合物。主要异构体是通过在空间位阻较小的碳原子上加成形成的。同样，3,3,5-三甲基环己酮肟的E和Z异构体的曼尼希缩合在两个亚甲基上发生反应，并且氨甲基片段的加成优先发生在更靠近肟羟基的亚甲基上。
• IMINOXYTRIAZINES AS RADICAL GENERATORS
  申请人：BASF SE

  公开号：US20150284604A1

  公开（公告）日：2015-10-08

  Iminoxytriazine compounds of the formula I wherein n is 1 or 2; R 1 and R 2 independently of each other are hydrogen, NH 2 , NHR 5 , NR 5 R 6 , COR 5 , COOR 5 , CONH 2 , CONHR 5 , CONR 5 R 6 , CN, SR 5 , OR 5 , C 1 -C 18 alkyl, C 3 -C 12 cycloalkyl, C 6 -C 14 aryl or C 2 -C 14 heteroaryl, wherein said C 3 -C 12 cycloalkyl, C 6 -C 14 aryl or C 2 -C 14 heteroaryl is unsubstituted or substituted by one or more radicals selected from the group consisting of C 1 -C 12 alkyl, C 3 -C 12 -cycloalkyl, phenyl, halogen and C 1 -C 12 alkoxy, or R 1 and R 2 together with the C atom to which they are linked form a 4 to 12 membered carbocyclic or heterocyclic saturated or unsaturated ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of C 1 -C 12 alkyl, C 3 -C 12 -cycloalkyl, phenyl, halogen and C 1 -C 12 alkoxy; R 3 is F, Cl, OH, OR 5 , SH, SR 5 , NH 2 , NHR 5 , NR 5 R 6 or R 1 R 2 C═N—O—; wherein R 1 and R 2 in all groups R 1 R 2 C═N—O— in the compound of the formula I are identical or different; if n is 1, R 4 is F, Cl, OH, OR 5 , SH, SR 5 , NH 2 , NHR 5 , NR 5 R 6 or R 1 R 2 C═N—O—; wherein R 1 and R 2 in all groups R 1 R 2 C═N—O— in the compound of the formula I are identical or different; if n is 2, R 4 is a difunctional group derived from a diol, diamine, aminoalcohol or mercaptoalcohol; R 5 and R 6 independently of each other are C 1 -C 18 alkyl, C 3 -C 12 cycloalkyl, C 6 -C 14 aryl or C 2 -C 14 heteroaryl; are suitable as radical generating agents.

  公式I中的亚硝基三嗪化合物，其中n为1或2；R1和R2独立地为氢、NH2、NHR5、NR5R6、COR5、COOR5、CONH2、CONHR5、CONR5R6、CN、SR5、OR5、C1-C18烷基、C3-C12环烷基、C6-C14芳基或C2-C14杂芳基，其中所述的C3-C12环烷基、C6-C14芳基或C2-C14杂芳基未取代或取代为来自C1-C12烷基、C3-C12环烷基、苯基、卤素和C1-C12烷氧基的一个或多个基团；或者R1和R2与它们连接的C原子一起形成一个4到12个成员的碳环或杂环，该碳环或杂环未取代或取代为来自C1-C12烷基、C3-C12环烷基、苯基、卤素和C1-C12烷氧基的一个或多个基团；R3为F、Cl、OH、OR5、SH、SR5、NH2、NHR5、NR5R6或R1R2C═N—O—；其中在公式I中的所有R1R2C═N—O—基团中，R1和R2相同或不同；如果n为1，则R4为F、Cl、OH、OR5、SH、SR5、NH2、NHR5、NR5R6或R1R2C═N—O—；其中在公式I中的所有R1R2C═N—O—基团中，R1和R2相同或不同；如果n为2，则R4为来自二元醇、二胺、氨基醇或巯基醇的二官能团；R5和R6独立地为C1-C18烷基、C3-C12环烷基、C6-C14芳基或C2-C14杂芳基；适用于产生基团的生成剂。
• HUTCHINS, R. O.;SU, WEI-YANG;SIVAKUMAR, R.;CISTONE, F.;STERCHO, Y. P., J. ORG. CHEM., 1983, 48, N 20, 3412-3422
  作者：HUTCHINS, R. O.、SU, WEI-YANG、SIVAKUMAR, R.、CISTONE, F.、STERCHO, Y. P.

  DOI：——

  日期：——
• US9255217B2
  申请人：——

  公开号：US9255217B2

  公开（公告）日：2016-02-09