5,6β-dibromo-5α-cholestan-3-one | 2515-09-5

• 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
• 英文名称: 5,6β-dibromo-5α-cholestan-3-one
• 英文别名: 5,6β-dibromo-5α-cholestanone-(3)；5,6β-Dibrom-5α-cholestanon-(3)；(5R,6R,8S,9S,10R,13R,14S,17R)-5,6-dibromo-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,4,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 2515-09-5
• 化学式: C₂₇H₄₄Br₂O
• 分子量: 544.454
• InChiKey: RMQXJLCPVCCLRY-HTTNMUSBSA-N

物化性质

• 熔点：
  79-80 °C
• 沸点：
  531.6±40.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,6β-dibromo-5α-cholestan-3-one 在 甲醇 、 硫酸 、 锌 作用下， 生成 4-胆甾烯-3-酮
  参考文献：
  名称：

  藻红蛋白。细胞摄取和定位，光敏化和光谱评估的机理。

  摘要：

  目的通过研究叶绿素的细胞吸收和细胞内定位模式及其在中国仓鼠肺成纤维细胞（V79）中的光谱特性，阐明叶绿素的光生物学行为。方法将菊红素稀释在二甲基亚砜（DMSO）中。使用配备有红敏光电倍增管的发光光谱仪测量荧光发射光谱和激发光谱。将V79细胞单层培养，并用0.25 microg / ml叶绿素标记，以用于摄取，细胞存活和细胞内定位研究。为了进行细胞存活和细胞内定位研究，随后将细胞以9.0 mW / cm2的通量率暴露于蓝光下。结果叶绿素在DMSO中的荧光激发光谱的特征是Soret谱带在418 nm处有最大峰。荧光发射光谱在643和706nm处具有峰。细胞中相应的光谱分别红移至422、650和712 nm。温育约10小时后，叶绿素的细胞吸收完成。摄取，活化能以及使用叶绿素在37摄氏度和0摄氏度下使用荧光显微镜观察的细胞分析表明，染料是通过扩散介导的途径吸收到细胞中的。叶绿素处理过的细胞曝光后，

  DOI：

  10.1080/00480169.2002.36291
• 作为产物：
  描述：

  cholesterol 在 potassium permanganate 、 乙醚 、 硫酸 、 溴 、 溶剂黄146 、 苯 作用下， 生成 5,6β-dibromo-5α-cholestan-3-one
  参考文献：
  名称：

  Windaus, Chemische Berichte, 1906, vol. 39, p. 518,521

  摘要：

  DOI：

文献信息

• A Novel Strategy for the Synthesis of Bromo-Substituted Cholestenone and its New Application to a Synthesis of 1α-Hydroxycholesterol
  作者：Bin Sun、Can Jin、Weike Su

  DOI：10.3184/174751916x14652251037643

  日期：2016.7

  bromo-substituted cholestenone, including 6β-bromocholestenone and 2α,6β-dibromocholestenone. The key step in this synthesis is a very mild method for the transformation of 5α,6β-dibromocholesterol into the 6β-bromocholestenone by treatment with NaClO/NaBr/TEMPO, followed by dehydro-bromination with Et3N. Bromination at C-2 with NBS/BPO (benzoyl peroxide) gave the 2α,6β-dibromo cholestenone. This was used

  开发了一种新型高效的溴代胆甾酮的制备方法，包括6β-溴胆甾酮和2α,6β-二溴胆甾酮。该合成的关键步骤是一种非常温和的方法，通过用 NaClO/NaBr/TEMPO 处理，然后用 Et3N 进行脱溴化氢，将 5α,6β-二溴胆固醇转化为 6β-溴胆甾酮。用 NBS/BPO（过氧化苯甲酰）在 C-2 处溴化得到 2α,6β-二溴胆甾酮。这用于合成 1α-羟基胆固醇。
• Characterization of Oxidative Stress in Various Tissues of Diabetic and Galactose-fed Rats
  作者：Robert M. Strother、Tonya G. Thomas、Mary Otsyula、Ruth A. Sanders、John B. Watkins III

  DOI：10.1155/edr.2001.211

  日期：——

  Rats fed a galactose-rich diet have been used for several years as a model for diabetes to study, particularly in the eye, the effects of excess blood hexoses. This study sought to determine the utility of galactosemia as a model for oxidative stress in extraocular tissues by examining biomarkers of oxidative stress in galactose-fed rats and experimentally-induced diabetic rats. Sprague-Dawley rats were divided into four groups: experimental control; streptozotocin-induced diabetic; insulin-treated diabetic; and galactose-fed. The rats were maintained on these regimens for 30 days, at which point the activities of catalase, glutathione peroxidase, glutathione reductase, and superoxide dismutase, as well as levels of lipid peroxidation and reduced and oxidized glutathione were determined in heart, liver, and kidney. This study indicates that while there are some similarities between galactosemic and diabetic rats in these measured indices of oxidative stress (hepatic catalase activity levels and hepatic and renal levels of oxidized glutathione in both diabetic and galactosemic rats were significantly decreased when compared to normal), overall the galactosemic rat model is not closely parallel to the diabetic rat model in extra-ocular tissues. In addition, several effects of diabetes (increased hepatic glutathione peroxidase activity, increased superoxide dismutase activity in kidney and heart, decreased renal and increased cardiac catalase activity) were not mimicked in galactosemic rats, and glutathione concentration in both liver and heart was affected in opposite ways in diabetic rats and galactose- fed rats. Insulin treatment reversed/prevented the activity changes in renal and cardiac superoxide dismutase, renal and cardiac catalase, and hepatic glutathione peroxidase as well as the hepatic changes in lipid peroxidation and reduced and oxidized glutathione, and the increase in cardiac glutathione. Thus, prudence should be exercised in the use of experimentally galactosemic rats as a model for diabetes until the correspondence of the models has been more fully characterized.

  喂食富含半乳糖饮食的大鼠多年来一直被用作糖尿病模型，以研究血液中过量己糖的影响，尤其是对眼部的影响。本研究试图通过检测喂食半乳糖的大鼠和实验诱导的糖尿病大鼠体内氧化应激的生物标志物，确定半乳糖血症作为眼外组织氧化应激模型的实用性。Sprague-Dawley 大鼠分为四组：实验对照组、链脲佐菌素诱导的糖尿病组、胰岛素治疗的糖尿病组和喂食半乳糖组。大鼠在这些方案下维持 30 天，然后测定心脏、肝脏和肾脏中过氧化氢酶、谷胱甘肽过氧化物酶、谷胱甘肽还原酶和超氧化物歧化酶的活性，以及脂质过氧化物和还原型及氧化型谷胱甘肽的水平。这项研究表明，虽然半乳糖血症大鼠和糖尿病大鼠在氧化应激的这些测量指标上有一些相似之处（与正常大鼠相比，糖尿病大鼠和半乳糖血症大鼠的肝脏过氧化氢酶活性水平以及肝脏和肾脏氧化谷胱甘肽水平都显著下降），但总体而言，半乳糖血症大鼠模型在眼外组织方面与糖尿病大鼠模型并不完全相同。此外，糖尿病的几种效应（肝脏谷胱甘肽过氧化物酶活性增加、肾脏和心脏超氧化物歧化酶活性增加、肾脏过氧化氢酶活性降低和心脏过氧化氢酶活性增加）在半乳糖血症大鼠中没有模拟出来，而且肝脏和心脏中的谷胱甘肽浓度在糖尿病大鼠和半乳糖喂养大鼠中受到了相反的影响。胰岛素治疗逆转/防止了肾脏和心脏超氧化物歧化酶、肾脏和心脏过氧化氢酶、肝脏谷胱甘肽过氧化物酶活性的变化，以及肝脏脂质过氧化、还原和氧化谷胱甘肽的变化和心脏谷胱甘肽的增加。因此，在对模型的对应关系进行更全面的描述之前，应谨慎使用实验性半乳糖血症大鼠作为糖尿病模型。
• Synthesis of Some New Arylmethylidene Steroidal Compounds
  作者：Mohammad Mushfiq、Geetesh Mudgal、Thressiamma Manuel、Afreen Shamim

  DOI：10.1039/a702999c

  日期：——

  An efficient method for the formation of new arylmethylidene steroidal compounds by the reaction of ketones with 4-(N,N-dimethylamino)benzaldehyde is described.

  描述了一种通过酮与 4-(N,N-二甲氨基) 苯甲醛反应形成新的芳基亚甲基甾体化合物的有效方法。
• Polyterpene und Polyterpenoide XCI. Zur präparativen Herstellung des Koprosterins, epi-Koprosterins und epi-Dihydro-cholesterins. Beitrag zur Kenntnis der räumlichen Lage der Hydroxylgruppe bei den Sterinen
  作者：L. Ruzieka、H. Brüngger、E. Eichenberger、Jules Meyer

  DOI：10.1002/hlca.193401701171

  日期：——
• Cholesterol and Companions. VII. Steroid Dibromides
  作者：Louis F. Fieser

  DOI：10.1021/ja01117a508

  日期：1953.11