1,4-胆固醇二烯-3-酮 | 4117-50-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 1,4-胆固醇二烯-3-酮
• 英文名称: cholesta-2,4-diene
• 英文别名: Δ^2,4-Cholestadiene；2,4-Cholestadien；cholestadiene-(2.4)；Cholestadien-(2.4)；Δ^2,4-Cholestadien；Cholesta-2,4-dien；(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-6,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene
• CAS: 4117-50-4
• 化学式: C₂₇H₄₄
• 分子量: 368.646
• InChiKey: BDJOURVDARTIRJ-HKQCOZBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,4-胆固醇二烯-3-酮 在 氯仿 、 乙酸乙酯 、 铂 作用下， 生成 4β,5-dihydroxy-5α-cholestane
  参考文献：
  名称：

  Ozone Formation in California's San Joaquin Valley: A Critical Assessment of Modeling and Data Needs

  摘要：

  Data from the 1990 San Joaquin Valley Air Quality Study/Atmospheric Utility Signatures, Predictions, and Experiments (SJVAQS/AUSPEX) field program in California's San Joaquin Valley (SJV) suggest that both urban and rural areas would have difficulty meeting an 8-hr average O-3 standard of 80 ppb. A conceptual model of O-3 formation and accumulation in the SJV is formulated based on the chemical, meteorological, and tracer data from SJVAQS/AUSPEX. Two major phenomena appear to lead to high O-3 concentrations in the SJV: (1) transport of O-3 and precursors from upwind areas (primarily the San Francisco Bay Area, but also the Sacramento Valley) into the SJV, affecting the northern part of the valley, and (2) emissions of precursors, mixing, transport (including lon,orange transport), and atmospheric reactions within the SJV responsible for regional and urban-scale (e.g., downwind of Fresno and Bakersfield) distributions of O-3. Using this conceptual model, we then conduct a critical evaluation of the meteorological model and air quality model. Areas of model improvements and data needed to understand and properly simulate O-3 formation in the SJV are highlighted.

  DOI：

  10.1080/10473289.2000.10464140
• 作为产物：
  描述：

  cholesterol 在 aluminum oxide 、 xylene 作用下， 生成 1,4-胆固醇二烯-3-酮
  参考文献：
  名称：

  Eck; Hollingsworth, Iowa State College Journal of Science, 1939, vol. 13, p. 329,332

  摘要：

  DOI：

文献信息

• Stereocontrolled formation of cis and trans ring junctions in hydrindane, decalin, and steroid systems by palladium-catalyzed regioselective and stereospecific hydrogenolysis of allylic formates
  作者：Tadakatsu Mandai、Takaji Matsumoto、Mikio Kawada、Jiro Tsuji

  DOI：10.1016/s0040-4020(01)87264-1

  日期：1993.1

  cis and trans ring junctions can be generated selectively in hydrindane, decalin and steroid systems by the palladium-catalyzed regioselective and stereospecific decarboxylation-hydrogenolysis of allylic formates. The trans junctions were formed from 3β allylic formates of decalin and steroid and 5β allylic formates of hydrindane. The corresponding 3α and 5α formates generate the cis ring junction.

  无论是顺式和反式环结可以选择性地氢化茚，萘烷和类固醇系统由烯丙基甲酸盐的钯催化的区域选择性和立体有择的脱羧-氢解来产生。所述反式结从十氢萘的3β烯丙基甲酸盐和类固醇和氢化茚的5β烯丙基甲酸盐形成。相应的3α和5α晶型生成顺式环结。
• Steroids and arynes. Part II. Some reactions of arynes with steroidal dienes and trienes
  作者：I. F. Eckhard、H. Heaney、B. A. Marples

  DOI：10.1039/j39690002098

  日期：——

  Steroid 5,7-dienes undergo the ene-reaction with benzyne and tetrachloro- and tetrafluoro-benzyen. Tetrafluoro-benzyne also forms a 5,8-adduct with a 5,7-diene and with a 5,7,9(11)-triene. Cholest-2,4-diene gives 1,4-adducts with benzyne and tetrafluorobenzyne. The pyrolyses of some adducts are discussed.

  甾类5，7-二烯与苯炔和四氯-和四氟-苯甲醛进行烯反应。四氟苯并ne还与5,7-二烯和5,7,9（11）-三烯形成5,8-加合物。Cholest-2,4-二烯与苯炔和四氟苯并生成1,4-加合物。讨论了一些加合物的热解。
• Reactions of iron pentacarbonyl with some steroid dienes
  作者：Howard Alper、John T. Edward

  DOI：10.1016/s0022-328x(00)87681-0

  日期：1968.10

  Tricarbonyliron complexes of steroidal Δ2,4- and Δ5,7-dienes have been prepared. The transoid Δ3,5- and Δ4,6-dienes, when heated with iron pentacarbonyl, rearrange to form the cisoid Δ2,4-diene complexes. Complex formation, followed by liberation of the diene ligand, thus offers a means of converting heteroannular steroidal dienes into their thermodynamically less stable homoannular isomers.

  甾体Δ的Tricarbonyliron络合物2,4 -和Δ 5,7 -dienes已经制备。所述transoidΔ 3,5 -和Δ 4,6 -dienes，当与五羰基铁加热，重新排列以形成cisoidΔ 2,4 -二烯配合物。形成复合物，随后释放二烯配体，因此提供了将异环类固醇二烯转化为其热力学上较不稳定的均环异构体的方法。
• Diene geometry and allylic axial chirality effect
  作者：Jacek Gawronski、Krystyna Gawronska

  DOI：10.1039/c39800000346

  日期：——

  The sense of the contribution of polarizable allylic axial bonds to the π–π* Cotton effect of dienes is found to be determined by the chirality of the system which is defined by the direction of the transition moment and direction of the allylic bond.

  发现可极化的烯丙基轴向键对π - π *二烯的棉效应的意义是由体系的手性决定的，该手性由跃迁矩的方向和烯丙基键的方向定义。
• A novel preparative method for homo- and heteroannular conjugated dienes in decalin derivatives by the palladium-catalyzed regioselective elimination reaction of allylic carbonates under mild conditions
  作者：Tadakatsu Mandai、Takaji Matsumoto、Yoshiki Nakao、Hisami Teramoto、Mikio Kawada、Jiro Tsuji

  DOI：10.1016/s0040-4039(00)92239-1

  日期：1992.4

  Homoannular conjugated dienes in decalin systems can be prepared by the palladium-catalyzed elimination reaction of α-allylic carbonates and heteroannular dienes are obtained from β-allylic carbonates.

  萘烷体系中的同环共轭二烯可以通过α-烯丙基碳酸酯的钯催化消除反应来制备，并且异环二烯由β-烯丙基碳酸酯获得。